Compound and Organic Light-Emitting Device Comprising the Same

Abstract

This specification provides a compound of Chemical Formula 1 and an organic light-emitting device comprising the same.

Description

Technical Field

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

[0002] This application claims the priority of Korean Patent Application No. 10-2020-0155405, filed with the Korean Patent Office on November 19, 2020, the entire contents of which are incorporated herein by reference. Background Art

[0003] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light-emitting device using the organic light-emitting phenomenon typically has a structure including an anode and a cathode and an organic layer located therebetween. Here, in order to improve the efficiency and stability of the organic light-emitting device, the organic layer is mostly formed of a multi-layer structure formed of different substances respectively. For example, it may 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 an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons transition back to the ground state.

[0004] There is a continuous demand for the development of new materials for improving the performance, lifespan, or efficiency of the organic light-emitting devices as described above. Summary of the Invention

[0005] Technical Problem

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

[0007] Solution to the Problem

[0008] One embodiment of this specification provides a compound represented by Chemical Formula 1 below.

[0009] [Chemical Formula 1]

[0010]

[0011] In Chemical Formula 1 above,

[0012] R1 to R4 are the same as or different from each other, and each independently is 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, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0013] a is an integer from 0 to 4, and when a is 2 or more, two or more R1s are the same as or different from each other,

[0014] b is an integer from 0 to 4. When the above-mentioned b is 2 or more, two or more R2s are each the same as or different from each other.

[0015] c is an integer from 0 to 4. When the above-mentioned c is 2 or more, two or more R3s are each the same as or different from each other.

[0016] d is an integer from 0 to 2. When the above-mentioned d is 2, the R4s are each the same as or different from each other.

[0017] L1 to L4 are each the same as or different from each other and are 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.

[0018] Ar3 is a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0019] Ar1 and Ar2 are each the same as or different from each other and are 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 of the following Chemical Formula 2. At least one of the above-mentioned Ar1 and Ar2 is a group of the following Chemical Formula 2.

[0020] [Chemical Formula 2]

[0021]

[0022] In the above Chemical Formula 2,

[0023] R5 is 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.

[0024] e is an integer from 0 to 3. When the above-mentioned e is 2 or more, two or more R5s are each the same as or different from each other.

[0025] In addition, one embodiment of the present specification provides an organic light-emitting device, which includes: 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 above-mentioned organic layers contain the above-mentioned compound.

[0026] Advantages of the Invention

[0027] The compounds described in this specification can be used as materials for the organic layer of an organic light-emitting device. When manufacturing an organic light-emitting device containing the compound according to an embodiment of the present invention, an organic light-emitting device with excellent luminous efficiency, low driving voltage, high efficiency, and long lifespan can be obtained.

[0028] In particular, when the compound of the present invention is used in a hole injection layer, a hole transport layer, or an electron blocking layer, the driving voltage of the device is reduced. In addition, effects such as increased efficiency and extended lifespan of the device can be obtained. Brief Description of the Drawings

[0029] Figure 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 illustrated.

[0030] Figure 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 illustrated.

[0031] Figure 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 suppression layer 10, a layer 11 that simultaneously performs electron transport and electron injection, and a cathode 4 is illustrated.

[0032] Description of Reference Signs

[0033] 1: Substrate

[0034] 2: Anode

[0035] 3: Light-emitting layer

[0036] 4: Cathode

[0037] 5: Hole injection layer

[0038] 6: Hole transport layer

[0039] 7: Light-emitting layer

[0040] 8: Electron transport layer

[0041] 9: Electron blocking layer

[0042] 10: Hole suppression layer

[0043] 11: Layer that simultaneously performs electron transport and electron injection. Detailed Description of the Invention

[0044] Hereinafter, this specification will be described in more detail.

[0045] The present specification provides a compound of the following chemical formula 1. The compound of the following chemical formula 1 is substituted with an amine group at the 2nd position of fluorene, at least one of Ar1 and Ar2 is substituted with a group of chemical formula 2, and at the 3rd position of fluorene, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is provided, and the HOMO and LUMO energy levels of the compound are adjusted, thereby adjusting the energy barrier between each organic layer.

[0046] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0047] In the present specification, when it is indicated that a certain part “includes / comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0048] Throughout the specification of the present application, the term "combination thereof" included in the expression of Markush form means a mixture or combination of one or more components selected from the expression of Markush form, and means that one or more components selected from the above components are included.

[0049] Hereinafter, the substituents in the present specification will be described in detail, but are not limited thereto.

[0050] In this manual, It indicates a site that bonds to other substituents or bonding parts.

[0051] In this specification, the term "substituted" refers to the replacement of a hydrogen atom bonded to a carbon atom of a compound with another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0052] In the present specification, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted 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 connecting two or more substituents among the substituents exemplified above, or has no substituent.

[0053] In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0054] In this specification, the above-mentioned alkyl group may be linear, branched or cyclic, and there is no particular limitation on the number of carbon atoms, but it is preferably 1 to 50. According to one embodiment, the number of carbon atoms of the above-mentioned alkyl group is 1 to 40. According to another embodiment, the number of carbon atoms of the above-mentioned alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 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-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0055] In this specification, the above-mentioned alkenyl group may be linear or branched, and there is no particular limitation on the number of carbon atoms, but it is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the above-mentioned alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above-mentioned alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbenyl, styryl, etc., but are not limited thereto.

[0056] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is 3 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is 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-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., but are not limited thereto.

[0057] In the present specification, the above-mentioned alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyl oxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.

[0058] The alkyl groups, alkoxy groups, and other substituents containing an alkyl moiety described in the present specification include all linear or branched forms.

[0059] In the present specification, the amino group may be selected from -NH2, monoalkylamino, dialkylamino, N-alkylarylamino, monoarylamino, diarylamino, triarylamino, N-arylheteroarylamino, N-alkylheteroarylamino, monoheteroarylamino, and diheteroarylamino. The number of carbon atoms is not particularly limited, but preferably it is 1 to 30. Specific examples of the amino group include methylamino, dimethylamino, trimethylamino, ethylamino, diethylamino, triethylamino, phenylamino, naphthylamino, biphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, xylidino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrylamino, N-biphenylphenanthrylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrylfluorenylamino, N-biphenylfluorenylamino, etc., but are not limited thereto.

[0060] In the present specification, the silyl group may be represented by the chemical formula -SiY a Y b Y c wherein the above-mentioned Y a 、Y b and Y c may each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0061] In this specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the above aryl group, as the monocyclic aryl group, it may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, etc., but is not limited thereto. As the above polycyclic aryl group, it may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, -yl group, a fluorenyl group, a triphenylenyl group, etc., but is not limited thereto.

[0062] In this specification, the above fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure.

[0063] When the above fluorenyl group is substituted, it may be (spirofluorenyl) and (spirobifluorenyl), (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and other substituted fluorenyl groups. However, it is not limited thereto.

[0064] The above aryl group may be substituted with an alkyl group and function as an arylalkyl group. The above alkyl group may be selected from the above examples.

[0065] In this specification, the heteroaryl group is an aromatic ring group containing one or more non-carbon atoms, that is, heteroatoms. Specifically, the above heteroatoms may include one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to one embodiment, the heteroaryl group has 2 to 30 carbon atoms. The above heteroaryl group may be monocyclic or polycyclic. As examples of the heteroaryl group, there are thiophenyl group, furyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, diazolyl group, pyridyl group, pyrimidinyl group, triazinyl group, triazolyl group, quinolinyl group, quinazolinyl group, carbazolyl group, benzo oxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuryl group, phenanthroline, iso oxazolyl group, thiadiazolyl group, naphthobenzofuryl group, dibenzofuryl group, etc., but is not limited thereto.

[0066] In this specification, the arylene group refers to a group having two bonding positions on the aryl group, that is, a divalent group. Except that they are each divalent groups, the above description of the aryl group can be applied.

[0067] In this specification, a heteroarylene group refers to a group having two bonding positions on a heteroaryl group, that is, a divalent group. Except for being divalent groups respectively, the descriptions of the above-mentioned heteroaryl groups can be applied to them.

[0068] In one embodiment of this specification, the above-mentioned R1 to R4 are the same as or different from each other, and each independently is 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, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0069] In one embodiment of this specification, the above-mentioned R1 to R4 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 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.

[0070] In one embodiment of this specification, the above-mentioned R1 to R4 are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0071] In one embodiment of this specification, the above-mentioned R1 to R4 are the same as or different from each other, and each independently is hydrogen or deuterium.

[0072] In one embodiment of this specification, the above-mentioned R1 to R4 are hydrogen.

[0073] In one embodiment of this specification, the above-mentioned a is an integer from 0 to 4. When the above-mentioned a is 2 or more, two or more R1s are the same as or different from each other.

[0074] In one embodiment of this specification, the above-mentioned R1 is hydrogen and the above-mentioned a is 4.

[0075] In one embodiment of this specification, the above-mentioned b is an integer from 0 to 4. When the above-mentioned b is 2 or more, two R2s are the same as or different from each other.

[0076] In one embodiment of this specification, the above-mentioned R2 is hydrogen and the above-mentioned b is 4.

[0077] In one embodiment of this specification, the above-mentioned c is an integer from 0 to 4. When the above-mentioned c is 2 or more, two R3s are the same as or different from each other.

[0078] In one embodiment of this specification, the above-mentioned R3 is hydrogen and the above-mentioned c is 4.

[0079] In one embodiment of the present specification, d is an integer from 0 to 2, and when b is 2, the two R4s are each the same as or different from each other.

[0080] In one embodiment of the present specification, R4 is hydrogen and d is 2.

[0081] In one embodiment of the present specification, L1 to L4 are each the same as or different from each other and are each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms. In one embodiment of the present specification, L1 to L4 are each the same as or different from each other and are each 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 triphenylene group, or a substituted or unsubstituted fluorenylene group.

[0082] In one embodiment of the present specification, L1 to L4 are each the same as or different from each other and are each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0083] In one embodiment of the present specification, L1 is a direct bond, or a substituted or unsubstituted phenylene group.

[0084] In one embodiment of the present specification, L1 is a direct bond or a phenylene group.

[0085] In one embodiment of the present specification, L1 is a direct bond.

[0086] In one embodiment of the present specification, L2 to L4 are each the same as or different from each other and are each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0087] In one embodiment of the present specification, L2 to L4 are each the same as or different from each other and are each 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 triphenylene group, or a substituted or unsubstituted fluorenylene group.

[0088] In one embodiment of the present specification, L2 to L4 are each the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0089] In one embodiment of the present specification, L2 to L4 are each the same as or different from each other and are each independently a direct bond, a phenylene group or a biphenylene group.

[0090] In one embodiment of the present specification, Ar3 is a substituted or unsubstituted amino 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.

[0091] In one embodiment of the present specification, Ar3 is a substituted or unsubstituted diarylamino group, a substituted or unsubstituted triarylamino 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.

[0092] In one embodiment of the present specification, Ar3 is a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted triphenylamino 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.

[0093] In one embodiment of the present specification, Ar3 is a diphenylamino group, a triphenylamino group, a phenyl group substituted or unsubstituted by butyl, a biphenyl group, a terphenyl group, a naphthyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

[0094] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or a group of the above Chemical Formula 2, and at least one of Ar1 and Ar2 is a group of the above Chemical Formula 2.

[0095] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or a group of the above Chemical Formula 2, and at least one of Ar1 and Ar2 is a group of the above Chemical Formula 2.

[0096] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently is a substituted or unsubstituted methyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a group of Formula 2 above, and at least one of Ar1 and Ar2 is a group of Formula 2 above.

[0097] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently is a tert-butyl group, an adamantyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group substituted or unsubstituted with a phenyl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spirobifluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group substituted or unsubstituted with a phenyl group, or a group of Formula 2 above, and at least one of Ar1 and Ar2 is a group of Formula 2 above.

[0098] In one embodiment of the present specification, R5 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0099] In one embodiment of the present specification, R5 is hydrogen or deuterium.

[0100] In one embodiment of the present specification, R5 is hydrogen.

[0101] In one embodiment of the present specification, R5 is hydrogen and c is 3.

[0102] In one embodiment of the present specification, the compound of Formula 1 can be represented by any one of the following compounds.

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] The compound of Chemical Formula 1 in this specification can be used to manufacture a nuclear structure through the reaction formula shown below. The substituents can be combined by methods known in the art, and the type, position, or number of substituents can be changed according to techniques known in the art.

[0125] <Reaction Formula 1>

[0126]

[0127] <Reaction Formula 2>

[0128]

[0129] In the above Reaction Formulas 1 and 2, the definitions of R1 to R5, Ar1 to Ar3, L1 to L4, a, b, c, and d are the same as those in Chemical Formulas 1 and 2 above.

[0130] In the above Reaction Formulas 1 and 2, X and Y can each be a halogen group such as Cl, Br, or I.

[0131] In this specification, by introducing various substituents into the nuclear structure as described above, compounds with various band gaps can be synthesized. In addition, in the present invention, by introducing various substituents into the nuclear structure of the structure shown above, the HOMO and LUMO energy levels of the compound can also be adjusted.

[0132] In addition, by introducing various substituents into the nuclear structure as described above, compounds with the inherent characteristics of the introduced substituents can be synthesized. For example, by introducing substituents of hole injection layer materials, hole transport materials, electron blocking materials, light-emitting layer materials, and electron transport layer materials mainly used in the manufacture of organic light-emitting devices into the above nuclear structure, substances that meet the conditions required in each organic layer can be synthesized.

[0133] In addition, the organic light-emitting device according to this specification is characterized by 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, and one or more of the organic layers contain the compound of Chemical Formula 1 mentioned above.

[0134] The organic light-emitting device of this specification forms one or more organic layers using the above compound. In addition, it can be manufactured using the manufacturing methods and materials of ordinary organic light-emitting devices.

[0135] When manufacturing an organic light-emitting device, the above compound can form an organic layer not only by vacuum evaporation but also by solution coating. Here, the so-called solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0136] The organic layer of the organic light-emitting device of this specification can be formed of a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of this 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, an electron injection layer, a layer that simultaneously performs electron transport and electron injection, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto, and it can include a smaller number or a larger number of organic layers.

[0137] In the organic light-emitting device of this specification, the above organic layer can include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer can contain the compound mentioned above.

[0138] In the organic light-emitting device of this specification, the above organic layer can include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer can contain the compound mentioned above.

[0139] In the organic light-emitting device of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the above-mentioned compound.

[0140] According to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may contain the above-mentioned compound as a dopant of the light-emitting layer.

[0141] In another embodiment, the organic layer includes a light-emitting layer, the light-emitting layer contains the above-mentioned compound as a dopant of the light-emitting layer, and may further contain a host.

[0142] In another embodiment, the organic layer includes a light-emitting layer, the light-emitting layer contains the above-mentioned compound as a dopant of the light-emitting layer, and contains a fluorescent host or a phosphorescent host, and may contain other organic compounds, metals or metal compounds as dopants.

[0143] As another example, the organic layer includes a light-emitting layer, the light-emitting layer contains the above-mentioned compound as a dopant of the light-emitting layer, and contains a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir)-based dopant.

[0144] According to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may contain the above-mentioned compound as a host of the light-emitting layer.

[0145] As another example, the organic layer includes a light-emitting layer, the light-emitting layer contains the above-mentioned compound as a host of the light-emitting layer, and may further contain a dopant.

[0146] In the organic light-emitting device of the present specification, the organic layer includes an electron blocking layer, and the electron blocking layer may contain the above-mentioned compound.

[0147] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0148] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0149] For example, the organic light-emitting device may have a stacked structure as shown below, but is not limited thereto.

[0150] (1) Anode / Hole transport layer / Light-emitting layer / Cathode

[0151] (2) Anode / Hole injection layer / Hole transport layer / Light-emitting layer / Cathode

[0152] (3) Anode / Hole transport layer / Light-emitting layer / Electron transport layer / Cathode

[0153] (4)Anode / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0154] (5)Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0155] (6)Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0156] (7)Anode / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0157] (8)Anode / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0158] (9)Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0159] (10)Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0160] (11)Anode / Hole Transport Layer / Light Emitting Layer / Hole Suppression Layer / Electron Transport Layer / Cathode

[0161] (12)Anode / Hole Transport Layer / Light Emitting Layer / Hole Suppression Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0162] (13)Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Suppression Layer / Electron Transport Layer / Cathode

[0163] (14)Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Suppression Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0164] (15)Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Hole Suppression Layer / Layer for Simultaneously Conducting Electron Transport and Electron Injection / Cathode

[0165] The structure of the organic light emitting device of this specification may have a structure as Figures 1 to 3 shown, but is not limited thereto.

[0166] Figure 1 The 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 illustrated. In the structure shown above, the above compound may be included in the above light emitting layer 3.

[0167] Figure 2Illustrated is the 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. In the structure as described above, the above compound may be included in the above hole injection layer 5, hole transport layer 6, light-emitting layer 7, or electron transport layer 8.

[0168] Figure 3 Illustrated is the 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 suppression layer 10, a layer 11 that simultaneously conducts electron transport and electron injection, and a cathode 4 are sequentially stacked on a substrate 1. In the structure as described above, the above compound may be included in the above hole transport layer 6 or electron blocking layer 9.

[0169] For example, the organic light-emitting device according to the present invention can be manufactured as follows: Using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is vapor-deposited on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, a hole suppression layer, and a layer that simultaneously conducts electron transport and electron injection is formed on the anode, and then a material that can be used as a cathode is vapor-deposited on the organic layer for manufacturing. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode material, an organic layer, and an anode material on a substrate.

[0170] The above organic layer may be a multilayer structure including a hole injection layer, a hole transport layer, a hole suppression layer, a layer that simultaneously conducts electron injection and electron transport, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously conducts hole injection and hole transport, etc., but is not limited thereto, and may also be a single-layer structure. In addition, the above organic layer can use various polymer materials and can be manufactured into a smaller number of layers by a solvent process other than the vapor deposition method, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer printing.

[0171] The above-mentioned anode is a hole-injecting electrode. As the anode material, generally, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferred. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), indium zinc oxide (IZO, Indium Zinc Oxide); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but not limited thereto.

[0172] The above-mentioned cathode is an electron-injecting electrode. As the cathode material, generally, in order to enable electrons to be easily injected into the organic layer, a material with a small work function is preferred. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multi-layer structure materials such as LiF / Al or LiO2 / Al, etc., but not limited thereto.

[0173] The above-mentioned hole injection layer serves to facilitate the injection of holes from the anode to the light-emitting layer. The hole injection material is a material that can well receive holes from the anode at a low voltage. It is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic compounds, hexanitrile hexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and conductive polymers such as polyaniline and polythiophene, etc., but not limited thereto.

[0174] The above-mentioned hole transport layer can serve to facilitate the transport of holes. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. A material with a large hole mobility is suitable. Specific examples include arylamine-based organic compounds, conductive polymers, and block copolymers having both a conjugated part and a non-conjugated part, etc., but not limited thereto.

[0175] The above-mentioned electron blocking layer refers to the following layer: formed on the above-mentioned hole transport layer, preferably disposed in contact with the light-emitting layer, and by adjusting the hole mobility, preventing the excessive migration of electrons to increase the recombination probability between holes and electrons, thereby improving the efficiency of the organic light-emitting device. The above-mentioned electron blocking layer contains an electron blocking substance. As an example of such an electron blocking substance, the compound of Chemical Formula 1 above, or an arylamine-based organic compound, etc. can be used, but it is not limited thereto.

[0176] The above-mentioned light-emitting layer can emit red, green or blue light and can be formed of a phosphorescent substance or a fluorescent substance. The above-mentioned light-emitting substance is a substance that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a substance with high quantum efficiency for fluorescence or phosphorescence. When the above-mentioned organic light-emitting device includes an additional light-emitting layer in addition to the light-emitting layer containing the compound of Chemical Formula 1 above, the additional light-emitting layer can emit red, green or blue light and can be formed of a phosphorescent substance or a fluorescent substance. As a specific example, there is aluminum tris(8-hydroxyquinoline) (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benz oxazole, benzothiazole and benzimidazole-based compounds; poly(p-phenylene vinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, etc., but not limited thereto.

[0177] As the host material of the light-emitting layer, there are aromatic condensed ring derivatives or heterocyclic-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 heterocyclic-containing compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds pyrimidine derivatives, etc., but not limited thereto.

[0178] A hole suppression layer can be provided between the above-mentioned electron transport layer and the light-emitting layer. The above-mentioned hole suppression layer is a layer that prevents holes from reaching the cathode and can generally be formed under the same conditions as the hole injection layer. Specifically, as the hole suppression substance, there are triazine derivatives, phenanthroline derivatives, etc., but not limited thereto, and materials known in the art can be used.

[0179] The above-mentioned electron transport layer can play a role in facilitating the transport of electrons. The electron transport substance is a substance that can receive electrons well from the cathode and transfer them to the light-emitting layer, and a substance with a large electron mobility is suitable. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, etc., but not limited thereto.

[0180] The above-mentioned electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferably used: compounds having the ability to transport electrons, having the effect of injecting electrons from the cathode, having an excellent electron injection effect on the light-emitting layer or the light-emitting material, preventing the excitons generated in the light-emitting layer from migrating to the hole injection layer, and having excellent thin film forming ability. Specifically, there are fluorenone, anthraquinodimethane, biphenylquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluoreneylidene methane, anthrone, etc. and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, etc., but are not limited thereto.

[0181] As the above-mentioned metal coordination compounds, 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), etc., but are not limited thereto.

[0182] According to the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0183] Hereinafter, in order to specifically illustrate this specification, experimental examples will be given for detailed description. However, the embodiments according to this specification can be deformed into various different forms, and are not construed as limiting the scope of the present application to the embodiments detailed below. The embodiments of the present application are provided to more completely illustrate this specification to those skilled in the art.

[0184] Modes for Carrying Out the Invention

[0185] <Synthesis Example>

[0186] Synthesis Example 1. Synthesis of Compound 1

[0187] Step 1) Synthesis of Compound 1-A

[0188]

[0189] To a mixture of 3-phenyl-9,9'-spirobi[fluorene]-2-amine (50.0 g, 122.69 mmol), 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (32.78 g, 122.69 mmol) and sodium tert-butoxide (NaOtBu, 16.51 g, 171.77 mmol) was added toluene (400 ml), and the mixture was heated with stirring for 10 minutes. To the above mixture was added 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium(II) (Pd(dppf)Cl2, 0.35 g, 0.61 mmol) dissolved in toluene (30 ml), and the mixture was heated with stirring for 1 hour. After completion of the reaction and filtration, liquid separation was carried out with chloroform and water. After removing the solvent, recrystallization was carried out with ethyl acetate to obtain the above compound 1-A (56.5 g, 77.55% yield).

[0190] Step 2) Synthesis of Compound 1

[0191]

[0192] To a mixture of the compound 1-A (20.0 g, 33.68 mmol) obtained in Step 1 of Synthesis Example 1 above, 4-bromo-1,1'-biphenyl (8.01 g, 34.35 mmol) and sodium tert-butoxide (4.53 g, 47.15 mmol) was added toluene (200 ml), and the mixture was heated with stirring for 10 minutes. To the above mixture was added bis(tri-tert-butylphosphine)palladium (BTP, 0.09 g, 0.17 mmol) dissolved in toluene (20 ml), and the mixture was heated with stirring for 1 hour. After completion of the reaction and filtration, liquid separation was carried out with toluene and water. After removing the solvent, recrystallization was carried out with ethyl acetate to obtain the above compound 1 (19.5 g, 77.61% yield). (MS [M+H] + = 746)

[0193] Synthesis Example 2. Synthesis of Compound 2

[0194]

[0195] Using the compound 1-A (20.0 g, 33.68 mmol) obtained in Step 1 of Synthesis Example 1 above and 1-(4-bromophenyl)naphthalene (9.73 g, 34.35 mmol), the above compound 2 (20.8 g, 77.58% yield) was obtained by the same method as in Step 2 of Synthesis Example 1 above. (MS [M+H] + = 796)

[0196] Synthesis Example 3. Synthesis of Compound 3

[0197]

[0198] Using the compound 1-A (20.0 g, 33.68 mmol) obtained in Step 1 of Synthesis Example 1 above and 2-bromo-9,9-dimethyl-9H-fluorene (9.38 g, 34.35 mmol), the above compound 3 (20.5 g, 77.43% yield) was obtained by the same method as in Step 2 of Synthesis Example 1 above. (MS [M+H] + = 786)

[0199] Synthesis Example 4. Synthesis of Compound 4

[0200]

[0201] Using the compound 1-A (20.0 g, 33.68 mmol) obtained in Step 1 of Synthesis Example 1 above and 4-bromodibenzo[b,d]furan (8.49 g, 34.35 mmol), the above compound 4 (20.0 g, 78.14% yield) was obtained by the same method as in Step 2 of Synthesis Example 1 above. (MS [M+H] + = 760)

[0202] Synthesis Example 5. Synthesis of Compound 5

[0203]

[0204] Using N-([1,1'-biphenyl]-4-yl)-3-phenyl-9,9'-spirobi[fluorene]-2-amine (20.0 g, 35.73 mmol) and 6-(4-chlorophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (10.89 g, 36.45 mmol), the above compound 5 (22.5 g, 76.60% yield) was obtained by the same method as in Step 2 of Synthesis Example 1 above. (MS [M+H] + = 822)

[0205] Synthesis Example 6. Synthesis of Compound 6

[0206] Step 1) Synthesis of Compound 6-A

[0207]

[0208] Using 3-phenyl-9,9'-spirobi[fluorene]-2-amine (50.0 g, 122.69 mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (33.52 g, 122.69 mmol), the above compound 6-A (57.0 g, 77.46% yield) was obtained by the same method as in Step 1 of Synthesis Example 1 above.

[0209] Step 2) Synthesis of Compound 6

[0210]

[0211] Using the compound 6-A (20.0 g, 33.46 mmol) obtained in Step 1 of Synthesis Example 6 above and 6-(4-chlorophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (10.13 g, 34.01 mmol), the above compound 6 (22.5 g, 77.99% yield) was obtained by the same method as in Step 2 of Synthesis Example 1 above. (MS [M+H] + = 862)

[0212] Synthesis Example 7. Synthesis of Compound 7

[0213] Step 1) Synthesis of Compound 7-A

[0214]

[0215] Using 3-([1,1'-biphenyl]-4-yl)-9,9'-spirobi[fluorene]-2-amine (50.0 g, 103.39 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (27.63 g, 103.39 mmol), the above compound 7-A (53.0 g, 76.52% yield) was obtained by the same method as in Step 1 of Synthesis Example 1 above.

[0216] Step 2) Synthesis of Compound 7

[0217]

[0218] Using the compound 7-A (20.0 g, 29.85 mmol) obtained in Step 1 of Synthesis Example 7 above and 4-bromo-1,1'-biphenyl (7.10 g, 30.45 mmol), the above compound 7 (19.2 g, 78.24% yield) was obtained by the same method as in Step 2 of Synthesis Example 1 above. (MS [M+H] + = 822)

[0219] Synthesis Example 8. Synthesis of Compound 8

[0220] Step 1) Synthesis of Compound 8-A

[0221]

[0222] Using 3-(dibenzo[b,d]furan-4-yl)-9,9'-spirobi[fluorene]-2-amine (50.0 g, 100.48 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (26.85 g, 100.48 mmol), the above compound 8-A (53.0 g, 77.13% yield) was obtained by the same method as in Step 1 of Synthesis Example 1 above.

[0223] Step 2) Synthesis of Compound 8

[0224]

[0225] Using the compound 8-A (20.0 g, 29.24 mmol) obtained in Step 1 of Synthesis Example 8 above and 4-bromo-1,1'-biphenyl (6.95 g, 29.83 mmol), the above compound 8 (19.0 g, 77.72% yield) was obtained by the same method as in Step 2 of Synthesis Example 1 above. (MS [M+H] + = 836)

[0226] Synthesis Example 9. Synthesis of Compound 9

[0227] Step 1) Synthesis of Compound 9-A

[0228]

[0229] Using 3-(4-(diphenylamino)phenyl)-9,9'-spirobi[fluorene]-2-amine (50.0 g, 87.00 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (23.25 g, 87.00 mmol), the above compound 9-A (52.5 g, 79.29% yield) was obtained by the same method as in Step 1 of Synthesis Example 1 above.

[0230] Step 2) Synthesis of Compound 9

[0231]

[0232] Using the compound 9-A (20.0 g, 26.28 mmol) obtained in Step 1 of Synthesis Example 9 above and 4-bromo-1,1'-biphenyl (6.25 g, 26.81 mmol), the above compound 9 (19.2 g, 80.00% yield) was obtained by the same method as in Step 2 of Synthesis Example 1 above. (MS [M+H] + = 913)

[0233] Synthesis Example 10. Synthesis of Compound 10

[0234]

[0235] To 3-phenyl-9,9'-spirobi[fluorene]-2-amine (15.0 g, 36.81 mmol), 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (20.16 g, 75.46 mmol), and sodium tert-butoxide (9.9 g, 103.07 mmol) was added xylene (200 ml), and the mixture was heated with stirring for 10 minutes. To the above mixture was added bis(tri-tert-butylphosphine)palladium(0) (0.15 g, 0.29 mmol) dissolved in xylene (20 ml), and the mixture was heated with stirring for 1 hour. After completion of the reaction and filtration, layer separation was carried out with toluene and water. After removing the solvent, recrystallization was carried out with ethyl acetate to obtain the above compound 10 (22.5 g, 78.35% yield). (MS [M+H] + = 780)

[0236] Synthesis Example 11. Synthesis of Compound 11

[0237]

[0238] Using 3-(4-(diphenylamino)phenyl)-9,9'-spirobi[fluorene]-2-amine (15.0 g, 26.05 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (14.27 g, 53.41 mmol), the above compound 11 (19.5 g, 79.02% yield) was obtained by the same method as in Synthesis Example 10 above. (MS [M+H] + = 947)

[0239] Synthesis Example 12. Synthesis of Compound 12

[0240]

[0241] Using N-([1,1'-biphenyl]-4-yl)-3-phenyl-9,9'-spirobi[fluorene]-2-amine (20.0 g, 35.73 mmol) and 5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (9.74 g, 36.45 mmol), the above compound 12 (20.8 g, 78.03% yield) was obtained by the same method as in Step 2 of Synthesis Example 1 above. (MS [M+H] + = 746)

[0242] Synthesis Example 13. Synthesis of Compound 13

[0243]

[0244] Using the compound 6-A (20.0 g, 33.36 mmol) obtained in Step 1 of Synthesis Example 6 above and 5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (9.09 g, 34.01 mmol), the above compound 13 (20.0 g, 75.65% yield) was obtained by the same method as in Step 2 of Synthesis Example 1 above. (MS [M+H] + = 786)

[0245] Synthesis Example 14. Synthesis of Compound 14

[0246]

[0247] Using 3-phenyl-9,9'-spirobi[fluorene]-2-amine (15.0 g, 36.81 mmol) and 5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (20.16 g, 75.46 mmol), the above compound 14 (22.5 g, 78.35% yield) was obtained by the same method as in Synthesis Example 10 above. (MS [M+H] + = 780)

[0248] Synthesis Example 15. Synthesis of Compound 15

[0249]

[0250] Using 3-(4-(diphenylamino)phenyl)-9,9'-spirobi[fluorene]-2-amine (15.0 g, 26.10 mmol) and 5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (14.30 g, 53.51 mmol), the above compound 15 (19.5 g, 78.87% yield) was obtained by the same method as in Synthesis Example 10 above. (MS [M+H] + = 947)

[0251] <Examples and Comparative Examples>

[0252] Example 1-1.

[0253] ITO (indium tin oxide) was used at The glass substrate whose thickness is coated into a film is placed in distilled water dissolved with detergent and washed using ultrasonic waves. At this time, the detergent used is a product of Fischer Co., and the distilled water used is the distilled water filtered twice using a filter manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing is carried out for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is carried out using a solvent of isopropyl alcohol, acetone, and methanol and then dried, and it is transported to a plasma cleaner. In addition, using oxygen plasma, the above substrate is cleaned for 5 minutes, and then the substrate is transported to a vacuum evaporator.

[0254] On the ITO transparent electrode prepared in this way, the compound represented by the following chemical formula HAT is thermally vacuum-evaporated with a thickness to form a hole injection layer. On the above hole injection layer, as a hole transport layer, the compound represented by the following chemical formula HT1 is vacuum-evaporated with a thickness, and then, as an electron blocking layer, the compound 1 manufactured in the above Synthesis Example 1 is thermally vacuum-evaporated with a thickness. Then, as a light-emitting layer, the compound represented by the following chemical formula BH and the compound represented by the following chemical formula BD are vacuum-evaporated with a thickness of 25:1 by weight ratio and with a thickness. Then, as a hole suppression layer, the compound represented by the following chemical formula HB1 is vacuum-evaporated with a thickness. Then, as a layer that simultaneously performs electron transport and electron injection, the compound represented by the following chemical formula ET1 and the compound represented by Liq are thermally vacuum-evaporated with a thickness of 1:1 by weight ratio and with a thickness. On the above layer that simultaneously performs electron transport and electron injection, lithium fluoride (LiF) is successively vacuum-evaporated with a thickness, and aluminum is vacuum-evaporated with a thickness to form a cathode, thereby manufacturing an organic light-emitting device.

[0255]

[0256] Experimental Examples 1-2 to 1-12 and Comparative Experimental Examples 1-1 to 1-4.

[0257] In the above Experimental Example 1-1, the compounds described in Table 1 below were used instead of Compound 1, and in other respects, the organic light-emitting devices of Experimental Examples 1-2 to 1-12 and Comparative Experimental Examples 1-1 to 1-4 were fabricated by the same method as in the above Experimental Example 1-1. A current density of 10 mA / cm was applied to the organic light-emitting devices fabricated in Experimental Examples 1-1 to 1-12 and Comparative Experimental Examples 1-1 to 1-4. 2When measuring the voltage, efficiency, color coordinates, and lifespan at a current of [value], the results are shown in Table 1 below. On the other hand, T95 represents the time required for the luminance to decrease from the initial luminance (6000 nits) to 95% at a current density of 10 mA / cm 2 of the current density.

[0258] [Table 1]

[0259]

[0260]

[0261] As shown in Table 1 above, it was confirmed that the compound of the present invention has excellent electron blocking ability, and the organic light-emitting device using it as the electron blocking layer shows remarkable effects in terms of driving voltage, efficiency, and lifespan.

[0262] In particular, when the bonding position of Ar3 is not the 3-position of the fluorene of the present invention but is bonded to other positions, when Ar1 or Ar2 is a group of the above Chemical Formula 2 and Ar3 is hydrogen, and when neither Ar1 nor Ar2 is a group of Chemical Formula 2, as well as when the bonding position of the amino group and the fluorene is different, it was confirmed that the effect is not good in terms of lifespan.

[0263] Experimental Examples 2-1 to 2-14 and Comparative Experimental Examples 2-1 to 2-4.

[0264] In the above Experimental Example 1-1, the compound represented by the above 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 Chemical Formula HT1 as the hole transport layer. Except for this, the organic light-emitting devices of Experimental Examples 2-1 to 2-14 and Comparative Experimental Examples 2-1 to 2-4 were fabricated by the same method as in the above Experimental Example 1-1. When applying a current of 10 mA / cm 2 to the organic light-emitting devices fabricated in the experimental examples and comparative experimental examples, the voltage, efficiency, color coordinates, and lifespan were measured, and the results are shown in Table 2 below. On the other hand, T95 represents the time required for the luminance to decrease from the initial luminance (6000 nits) to 95% at a current density of 10 mA / cm 2 of the current density.

[0265] [Table 2]

[0266]

[0267]

[0268] As shown in Table 2 above, it was confirmed that the compound of the present invention has excellent hole transport ability, and the organic light-emitting device using it as the hole transport layer showed remarkable effects in terms of driving voltage, efficiency, and lifetime.

Claims

1. A compound of the following Chemical Formula 1: Chemical Formula 1 In the Chemical Formula 1, R1 to R4 are the same as or different from each other, and are each independently hydrogen or deuterium, a is an integer from 0 to 4. When a is 2 or more, two or more R1s are the same as or different from each other, b is an integer from 0 to 4. When b is 2 or more, two or more R2s are the same as or different from each other, c is an integer from 0 to 4. When c is 2 or more, two or more R3s are the same as or different from each other, d is an integer from 0 to 2. When d is 2, R4s are the same as or different from each other, L1 to L4 are the same as or different from each other, and are each independently a direct bond, or a substituted or unsubstituted arylene group, Ar3 is a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a group of the following Chemical Formula 2. At least one of Ar1 and Ar2 is a group of the following Chemical Formula 2, Chemical Formula 2 In the Chemical Formula 2, R5 is hydrogen or deuterium, e is an integer from 0 to 3. When e is 2 or more, two or more R5s are the same as or different from each other, wherein the term "substituted or unsubstituted" means being substituted by one or more substituents selected from deuterium, alkyl group, cycloalkyl group, aryl group, and heteroaryl group, or being substituted by a substituent formed by connecting two or more of the above substituents, or having no substituent.

2. The compound according to claim 1, wherein L1 to L4 are the same as or different from each other, and are each 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 triphenylene group, or a substituted or unsubstituted fluorenylene group, wherein the term "substituted or unsubstituted" means being substituted by one or more substituents selected from deuterium, alkyl group, cycloalkyl group, aryl group, and heteroaryl group, or being substituted by a substituent formed by connecting two or more of the above substituents, or having no substituent.

3. The compound according to claim 1, wherein, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or a group of the Chemical Formula 2. At least one of Ar1 and Ar2 is a group of the Chemical Formula 2, wherein the term "substituted or unsubstituted" means being substituted by one or more substituents selected from deuterium, alkyl group, cycloalkyl group, aryl group, and heteroaryl group, or being substituted by a substituent formed by connecting two or more of the above substituents, or having no substituent.

4. The compound according to claim 1, wherein Ar3 is a substituted or unsubstituted diarylamino group, a substituted or unsubstituted triarylamino 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, The term "substituted or unsubstituted" means being substituted by one or more substituents selected from deuterium, alkyl, cycloalkyl, aryl, and heteroaryl, or being substituted by a substituent formed by linking two or more of the said substituents, or having no substituent.

5. The compound according to claim 1, wherein The compound of the said Chemical Formula 1 is any one of the following compounds:

6. An organic light-emitting device, wherein, Including: A first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, and one or more of the organic layers contain the compound described in any one of Claims 1 to 5.

7. The organic light emitting device according to claim 6, wherein, The organic layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer contains the compound.

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