Heterocyclic compounds and organic light emitting devices comprising the same

Abstract

The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same. The present invention provides an organic light emitting device comprising: a first electrode; a second electrode disposed to face the first electrode; and one or more layers of an organic material disposed between the first electrode and the second electrode, wherein one or more of the layers of the organic material comprises a compound of structural formula: and wherein the layer of the organic material comprising the compound is an electron injection layer, an electron transport layer, or a layer that injects and transports electrons simultaneously. The compounds of the present invention can improve efficiency as well as improve low driving voltage and / or service life characteristics in organic light emitting devices.

Description

[0001] This application is a divisional application of the application with the application number 201580017744.7, the title of "Heterocyclic Compound and Organic Light Emitting Device Comprising the Same", the filing date of April 2, 2015 (PCT / KR2015 / 003291, entry into the national phase date of September 29, 2016) in the Korean Intellectual Property Office.

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2014-0040818, filed on April 4, 2014, Korean Patent Application No. 10-2015-0017929, filed on February 5, 2015, and Korean Patent Application No. 10-2015-0045586, filed on March 31, 2015, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. TECHNICAL FIELD

[0003] The present application relates to a heterocyclic compound and an organic light emitting device comprising the same. BACKGROUND

[0004] Generally, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy by using organic material. An organic light emitting device using the organic light emitting phenomenon typically has a structure including an anode, a cathode, and an organic material layer interposed therebetween. In this context, the organic material layer can have a multi-layer structure composed of different materials to improve the efficiency and stability of the organic light emitting device in many cases, and can be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of the organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer and electrons are injected from the cathode into the organic material layer, and when the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall to the ground state again.

[0005] There is an ongoing need to develop new materials for the above-described organic light emitting device. SUMMARY

[0006] TECHNICAL PROBLEM

[0007] The present specification describes a heterocyclic compound and an organic light emitting device comprising the same.

[0008] TECHNICAL SOLUTION

[0009] Exemplary embodiments of the present application provide a compound represented by the following formula 1:

[0010] [Formula 1]

[0011]

[0012] In formula 1,

[0013] Ar1and Ar2are the same as each other, and are phenyl, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl(sulfinyl) group, an aryl(sulfinyl) group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group; a biphenyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl(sulfinyl) group, an aryl(sulfinyl) group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group; a naphthyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl(sulfinyl) group, an aryl(sulfinyl) group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group; or a phenanthryl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl(sulfinyl) group, an aryl(sulfinyl) group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group,

[0014] L is a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group,

[0015] R1and R2are the same or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkyl(ene)sulfonyl group; a substituted or unsubstituted aryl(ene)sulfonyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted aralkenyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or can form, together with an adjacent group, a substituted or unsubstituted ring,

[0016] R3and R4are the same or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkyl(ene)sulfonyl group; a substituted or unsubstituted aryl(ene)sulfonyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted aralkenyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylphosphine group; or a substituted or unsubstituted phosphine oxide group; or can form, together with an adjacent group, a substituted or unsubstituted ring,

[0017] m is an integer of 1 to 5,

[0018] a is an integer of 0 to 3, and

[0019] b is an integer of 0 to 4, and

[0020] when m, a and b are each 2 or more, the structures in parentheses are the same or different from each other.

[0021] Further, one exemplary embodiment of the present application provides an organic light emitting device including: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound of Formula 1.

[0022] Advantageous Effects

[0023] The compounds described in the present specification can be used as a material for an organic material layer of an organic light emitting device. The compounds according to at least one exemplary embodiment can improve efficiency as well as low driving voltage and / or lifespan characteristics in an organic light emitting device. In particular, the compounds described in the present specification can be used as a material for hole injection, hole transport, hole injection and hole transport, light emission, electron transport, or electron injection. Further, the compounds described in the present specification can be preferably used as a material for a light emitting layer, electron transport, or electron injection, and more preferably as a material for electron transport or electron injection. BRIEF DESCRIPTION OF DRAWINGS

[0024] 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.

[0025] 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.

[0026] Figure 3 MS data results of the compound 67 prepared in the example are illustrated. DETAILED DESCRIPTION

[0027] Hereinafter, the present application will be described in more detail.

[0028] One exemplary embodiment of the present application provides a compound represented by Formula 1.

[0029] Examples of substituents will be described hereinafter, but are not limited thereto.

[0030] In the present specification, the term "substituted or unsubstituted" means that a group is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; an oxidized phosphonic group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkyl(ene)sulfinyl group; an aryl(ene)sulfinyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an arylphosphine group; and a heterocyclic group, or a substituent in which two or more substituents exemplified above are linked to each other is substituted or unsubstituted. For example, "a substituent in which two or more substituents are linked to each other" can be a biphenyl group. That is, the biphenyl group can also be an aryl group, and can be understood as a substituent in which two phenyl groups are linked to each other.

[0031] According to one exemplary embodiment of the present application, the term "substituted or unsubstituted" can preferably mean that a group is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; an alkyl group; an alkoxy group; and an aryl group.

[0032] According to one exemplary embodiment of the present application, the compound represented by formula 1 can be unsubstituted or substituted with at least one deuterium.

[0033] In the present specification, "adjacent" groups can mean a substituent that substitutes an atom directly linked to an atom substituted by a corresponding substituent, a substituent disposed spatially closest to a corresponding substituent, or another substituent that substitutes an atom substituted by a corresponding substituent. For example, two substituents substituted at ortho positions of a benzene ring, and two substituents that substitute the same carbon in an aliphatic ring can be understood as groups "adjacent" to each other.

[0034] In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Particularly, the carbonyl group can be a compound having the following structure, but is not limited thereto.

[0035]

[0036] In the present specification, in the ester group, the oxygen of the ester group can be substituted with a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Particularly, the ester group can be a compound having the following structure, but is not limited thereto.

[0037]

[0038] In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Particularly, the imide group can be a compound having the following structure, but is not limited thereto.

[0039]

[0040] In the present specification, the silyl group can be represented by the formula -SiRR'R", and R, R', and R" can each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include 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 are not limited thereto.

[0041] In the present specification, the boron group can be represented by the formula -BRR'R", and R, R', and R" can each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the boron group include a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but are not limited thereto.

[0042] In the present specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

[0043] In the present specification, the alkyl group can be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 40. According to one exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to still another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a t-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a t-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, an n-octyl group, a t-octyl group, a 1-ethyl-propyl group, a 1,1-dimethyl-propyl group, an isohexyl group, a 4-methylhexyl group, a 5-methylhexyl group, and the like, but are not limited thereto.

[0044] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms therein is not particularly limited, but is preferably 2 to 40. According to one exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples of the alkenyl group 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-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, It includes, but is not limited to, styrene, etc.

[0045] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one exemplary embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 30. According to another exemplary embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 20. According to yet another exemplary embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 6. Specific examples include, but are not limited to, 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, etc.

[0046] In this specification, specific examples of the arylamine group include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, or substituted or unsubstituted triarylamine groups. The aryl group in the arylamine group may be a monocyclic aryl or a polycyclic aryl. The arylamine group comprising two or more aryl groups may comprise a monocyclic aryl, a polycyclic aryl, or both.

[0047] Specific examples of the arylamine group include, but are not limited to, phenylamine, naphthylamine, biphenylamine, anthraceneamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthraylamine, diphenylamine, phenylnaphthylamine, xylylamine, phenyltolylamine, carbazole, triphenylamine, etc.

[0048] In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted mono-heteroarylamine group, a substituted or unsubstituted di-heteroarylamine group, or a substituted or unsubstituted tri-heteroarylamine group. The heteroaryl group in the heteroarylamine group can be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group including two or more heterocyclic groups can include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or both a monocyclic heterocyclic group and a polycyclic heterocyclic group.

[0049] In the present specification, the arylheteroarylamine group refers to an amine group substituted with an aryl group and a heterocyclic group.

[0050] In the present specification, examples of the arylphosphine group include a substituted or unsubstituted mono-arylphosphine group, a substituted or unsubstituted di-arylphosphine group, or a substituted or unsubstituted tri-arylphosphine group. The aryl group in the arylphosphine group can be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine group including two or more aryl groups can include a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group.

[0051] In the present specification, examples of the arylamine group refer to a substituted or unsubstituted monocyclic di-arylamine group, a substituted or unsubstituted polycyclic di-arylamine group, or a substituted or unsubstituted monocyclic and polycyclic di-arylamine group.

[0052] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and can be a monocyclic aryl group or a polycyclic aryl group. According to one exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 20. When the aryl group is a monocyclic aryl group, examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto. Examples of the polycyclic aryl group include a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, In the present specification, the fluorenyl group can be substituted, and two substituents can be combined with each other to form a spiro structure.

[0053] In the present specification, the fluorenyl group can be substituted, and two substituents can be combined with each other to form a spiro structure.

[0054] When the fluorenyl group is substituted, the fluorenyl group can be , etc. However, the fluorenyl group is not limited thereto.

[0055] In the present specification, the heterocyclic group is a heterocyclic group including one or more of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include a thienyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, a triazolyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolyl group, a quinoxalyl group, a phthalazyl group, a pyridopyrimidyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, an olphinyl group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a dibenzofuranyl group, and the like, but is not limited thereto.

[0056] In the present specification, the description of the above-mentioned heterocyclic group is applicable to a heteroaryl group other than an aromatic group.

[0057] In the present specification, the description of the above-mentioned aryl group is applicable to an aryl group of aryloxy, arylthio, aryl (sulfinyl) group, aryl phosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, and arylheteroarylamine group.

[0058] In the present specification, the description of the above-mentioned alkyl group is applicable to an alkyl group of alkylthio, alkyl (sulfinyl) group, aralkyl group, aralkylamine group, alkylaryl group, and alkylamine group.

[0059] In the present specification, the description of the above-mentioned heterocyclic group is applicable to a heteroaryl group, a heteroarylamine group, and an arylheteroarylamine group.

[0060] In the present specification, the description of the above-mentioned alkenyl group is applicable to an alkenyl group of aralkenyl group.

[0061] In the present specification, the description of the above-mentioned aryl group is applicable to an arylene group other than a divalent arylene group.

[0062] In the present specification, the description of the above-mentioned heterocyclic group is applicable to an heteroarylene group other than a divalent heteroarylene group.

[0063] In the present specification, the meaning of forming a ring together with an adjacent group means forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocyclic ring; a substituted or unsubstituted aromatic heterocyclic ring; and a condensed ring thereof together with the adjacent group.

[0064] In the present specification, the aliphatic hydrocarbon ring means a ring composed of only carbon and hydrogen atoms, which is a ring that is not an aromatic group.

[0065] In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, an anthryl group, and the like, but are not limited thereto.

[0066] In the present specification, the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms.

[0067] In the present specification, the aromatic heterocycle refers to an aromatic ring including one or more heteroatoms.

[0068] In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle, and the aromatic heterocycle can be a single ring or a multiple ring.

[0069] According to one exemplary embodiment of the present application, Formula 1 can be represented by any one of the following Formulae 2 to 4.

[0070] [Formula 2]

[0071]

[0072] [Formula 3]

[0073]

[0074] [Formula 4]

[0075]

[0076] In Formulae 2 to 4,

[0077] Ar1, Ar2, L, R3, R4, a, b, and m are defined the same as defined in Formula 1,

[0078] R11, R12, R21, and R22 are defined the same as defined for R3 and R4,

[0079] X1and X2are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkyl(ene)sulfonyl group; a substituted or unsubstituted aryl(ene)sulfonyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted aralkenyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamine group; a substituted or unsubstituted arylphosphine group; or a substituted or unsubstituted phosphine oxide group; or can be taken together with an adjacent group to form a substituted or unsubstituted ring,

[0080] r11and r12are the same as or different from each other, and each independently an integer of 0 to 5,

[0081] r21and r22are the same as or different from each other, and each independently an integer of 0 to 4, and

[0082] When r11, r12, r21, and r22are each 2 or more, the structures in the parentheses are the same as or different from each other.

[0083] According to one exemplary embodiment of the present application, Formula 1 can be represented by any one of the following Formulae 5 to 8.

[0084] [Formula 5]

[0085]

[0086] [Formula 6]

[0087]

[0088] [Formula 7]

[0089]

[0090] [Formula 8]

[0091]

[0092] In Formulae 5 to 8,

[0093] Ar1, Ar2, L, R1to R4, m, a, and b are defined the same as defined in Formula 1.

[0094] According to an exemplary embodiment of the present application, Formula 2 can be represented by any one of the following Formula 2-1 to Formula 2-4.

[0095] [Formula 2-1]

[0096]

[0097] [Formula 2-2]

[0098]

[0099] [Formula 2-3]

[0100]

[0101] [Formula 2-4]

[0102]

[0103] In Formula 2-1 to Formula 2-4,

[0104] Ar1, Ar2, L, R3, R4, a, and b are the same as defined in Formula 1,

[0105] R11, R12, r11, and r12 are the same as defined in Formula 2.

[0106] According to an exemplary embodiment of the present application, Formula 3 can be represented by any one of the following Formula 3-1 to Formula 3-4.

[0107] [Formula 3-1]

[0108]

[0109] [Formula 3-2]

[0110]

[0111] [Formula 3-3]

[0112]

[0113] [Formula 3-4]

[0114]

[0115] In Formula 3-1 to Formula 3-4,

[0116] Ar1, Ar2, L, R3, R4, a, and b are the same as defined in Formula 1, and

[0117] R21, R22, r21, and r22 are the same as defined in Formula 3.

[0118] According to one exemplary embodiment of the present application, X1and X2are the same as or different from each other, and each is independently substituted or unsubstituted alkyl.

[0119] According to one exemplary embodiment of the present application, X1and X2are the same as or different from each other, and each is independently substituted or unsubstituted alkyl.

[0120] According to one exemplary embodiment of the present application, X1and X2are methyl.

[0121] According to one exemplary embodiment of the present application, Ar1and Ar2are the same as each other, and are phenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and alkyl; biphenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl and aryl; naphthyl, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl and aryl; or phenanthryl, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl and aryl.

[0122] According to one exemplary embodiment of the present application, Ar1and Ar2are the same as each other, and are phenyl, unsubstituted or substituted with deuterium; biphenyl, unsubstituted or substituted with deuterium; naphthyl, unsubstituted or substituted with deuterium; or phenanthryl, unsubstituted or substituted with deuterium.

[0123] According to one exemplary embodiment of the present application, Ar1and Ar2are the same as each other, and are phenyl, biphenyl, naphthyl or phenanthryl.

[0124] According to one exemplary embodiment of the present application, R1and R2are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkyl(thio) sulfoxyl group; an aryl(thio) sulfoxyl group; an alkenyl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an arylheteroarylamine group; an aryl phosphine group; a phosphine oxide group; an aryl group, unsubstituted or substituted with deuterium, an alkyl group or an alkoxy group; or a heterocyclic group, or can form a ring together with an adjacent group.

[0125] According to one exemplary embodiment of the present application, R1and R2are the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl, or combine with each other to form a substituted or unsubstituted ring.

[0126] According to an exemplary embodiment of the present application, R1and R2are the same as or different from each other, and each is independently hydrogen; deuterium; alkyl, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkyl(sulfinyl) group, aryl(sulfinyl) group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine group, heteroarylamine group, arylamine group, aryl phosphine group, and heterocyclic group; or aryl, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkyl(sulfinyl) group, aryl(sulfinyl) group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine group, heteroarylamine group, arylamine group, aryl phosphine group, and heterocyclic group, or combine with each other to form a ring, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkyl(sulfinyl) group, aryl(sulfinyl) group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine group, heteroarylamine group, arylamine group, aryl phosphine group, and heterocyclic group.

[0127] According to an exemplary embodiment of the present application, R1and R2are the same as or different from each other, and each is independently hydrogen; deuterium; alkyl, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl, alkoxy, and aryl; or aryl, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl, alkoxy, and aryl, or combine with each other to form a ring, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl, alkoxy, and aryl.

[0128] According to an exemplary embodiment of the present application, R1and R2are the same as or different from each other, and each is independently hydrogen; alkyl; or aryl, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, alkyl, and alkoxy, or combine with each other to form a ring.

[0129] According to an exemplary embodiment of the present application, R1and R2are the same as or different from each other, and each is independently substituted or unsubstituted alkyl; or substituted or unsubstituted monocyclic to tricyclic aryl, or combine with each other to form a substituted or unsubstituted ring.

[0130] According to an exemplary embodiment of the present application, R1and R2are the same as or different from each other, and each is independently substituted or unsubstituted alkyl; or substituted or unsubstituted phenyl, or combine with each other to form a substituted or unsubstituted ring.

[0131] According to an exemplary embodiment of the present application, R1and R2are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, alkyl, and aryl, or combine with each other to form a ring.

[0132] According to an exemplary embodiment of the present application, R1and R2are the same as or different from each other, and each is independently alkyl; and aryl, or combine with each other to form a ring.

[0133] According to an exemplary embodiment of the present application, R1and R2are the same as or different from each other, and each is independently alkyl; or phenyl, or combine with each other to form a ring.

[0134] According to an exemplary embodiment of the present application, R1and R2are the same as or different from each other, and each is independently methyl; or phenyl, or combine with each other to form a ring.

[0135] According to an exemplary embodiment of the present application, R3and R4are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a silyl group; a boron group; alkyl; cycloalkyl; alkoxy; aryloxy; alkylthio; arylthio; alkyl(ene)sulfinyl; aryl(ene)sulfinyl; alkenyl; aralkyl; aralkenyl; alkylaryl; alkylamino; aralkylamino; arylphosphine; or phosphine oxide group.

[0136] According to an exemplary embodiment of the present application, R3and R4are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, or alkyl.

[0137] According to an exemplary embodiment of the present application, R3and R4are hydrogen.

[0138] According to an exemplary embodiment of the present application, R4is hydrogen.

[0139] According to an exemplary embodiment of the present application, R3is hydrogen.

[0140] According to an exemplary embodiment of the present application, L is phenylene, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl(ylidene)sulfonyl group, an aryl(ylidene)sulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an aryl phosphine group, and a heterocyclic group; or biphenylene, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl(ylidene)sulfonyl group, an aryl(ylidene)sulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an aryl phosphine group, and a heterocyclic group.

[0141] According to an exemplary embodiment of the present application, L is phenylene; or biphenylene.

[0142] According to an exemplary embodiment of the present application, L can be selected from any one of the following structures.

[0143]

[0144]

[0145] The structure can be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkyl(ylidene)sulfonyl group; an aryl(ylidene)sulfonyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an aryl phosphine group; and a heterocyclic group.

[0146] According to an exemplary embodiment of the present application, the may be selected from any one of the following structures.

[0147]

[0148]

[0149] In the structure,

[0150] R1and R2are the same as defined in Formula 1, and

[0151] The structure can be unsubstituted or substituted with one or more substituents selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkyl(sulfinyl) group; an aryl(sulfinyl) group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an aryl phosphine group; and a heterocyclic group.

[0152] According to one exemplary embodiment of the present application, m is 1.

[0153] According to one exemplary embodiment of the present application, m is 1 or 2.

[0154] According to one exemplary embodiment of the present application, the compound of Formula 1 can be any one selected from the following compounds:

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165] The compound represented by Formula 1 can be prepared based on the Preparation Examples to be described below. According to one exemplary embodiment, the compound can be prepared by, for example, the following Reaction Scheme 1.

[0166] [Reaction Scheme 1]

[0167]

[0168] In Reaction Scheme 1,

[0169] Ar1, Ar2, L, R1, R2, R3, R4, a, b, and m are the same as in Formula 1.

[0170] In particular, according to one exemplary embodiment of the present application, the compound of Formula 1 can be prepared by coupling a compound of a halogen-substituted triazine derivative with an aromatic compound substituted with a boronic acid or a boronic acid derivative using a palladium catalyzed reaction.

[0171] Also, the present application provides an organic light emitting device including a compound represented by any one of Formulae 1 to 8.

[0172] One exemplary embodiment of the present application provides an organic light emitting device including: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers include a compound of any one of Formulae 1 to 8.

[0173] The organic material layers of the organic light emitting device of the present application can also consist of a single layer structure or a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present application can have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as the organic material layers. However, the structure of the organic light emitting device is not limited thereto, and can include a smaller number of organic layers.

[0174] In one exemplary embodiment of the present application, the organic material layers include a hole injection layer, a hole transport layer, or a layer that simultaneously transports and injects holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously transports and injects holes includes the compound of Formula 1.

[0175] In another exemplary embodiment, the organic material layers include a light emitting layer, and the light emitting layer includes the compound of Formula 1.

[0176] According to one exemplary embodiment of the present application, the organic material layers include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound of any one of Formulae 1 to 8.

[0177] In one exemplary embodiment of the present application, the electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons includes the compound of Formula 1.

[0178] In another exemplary embodiment, the organic material layers include a light emitting layer and an electron transport layer, and the electron transport layer includes a compound of any one of Formulae 1 to 8.

[0179] In still another exemplary embodiment, the organic light emitting device can be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate (normal type).

[0180] In still another exemplary embodiment, the organic light emitting device can be an organic light emitting device having a reverse structure (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

[0181] For example, the structure of an organic light emitting device according to one exemplary embodiment of the present application is illustrated in Figure 1 and Figure 2

[0182] 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. In the structure, the compound can be included in the light emitting layer.

[0183] 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. In the structure, the compound can be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

[0184] The organic light emitting device of the present application can be manufactured by materials and methods known in the art, with the difference that one or more of the organic material layers includes the compound of the present application, i.e., the compound of any one of Formula 1 to Formula 8.

[0185] When the organic light emitting device includes a plurality of organic material layers, the organic material layers can be formed of the same material or different materials.

[0186] One exemplary embodiment of the present application is an organic light emitting device including a first electrode; a second electrode disposed to face the first electrode; a light emitting layer disposed between the first electrode and the second electrode; and two or more organic material layers disposed between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the heterocyclic compound. In one exemplary embodiment, as the two or more organic material layers, two or more can be selected from an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer.

[0187] In one exemplary embodiment of the present application, the organic material layers include two or more electron transport layers, and at least one of the two or more electron transport layers includes the heterocyclic compound. In particular, in one exemplary embodiment of the present application, the heterocyclic compound can also be included in one of the two or more electron transport layers, and can be included in each of the two or more electron transport layers.​

[0188] In addition, in one exemplary embodiment of the present application, other materials than the heterocyclic compound can be the same as or different from each other when the heterocyclic compound is contained in each of the two or more electron transport layers.

[0189] The organic light emitting device of the present application can be manufactured by materials and methods known in the art, with the difference that one or more of the organic material layers comprises the compound of any one of Formulae 1 to 8, i.e., the compound represented by any one of Formulae 1 to 8.

[0190] For example, the organic light emitting device of the present application can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device can be manufactured by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode by a physical vapor deposition (PVD) method using, for example, sputtering or electron beam evaporation, forming an organic material layer comprising a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material which can be used as a cathode thereon. In addition to the above method, the organic light emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0191] Further, when the organic light emitting device is manufactured, the compound of any one of Formulae 1 to 8 can be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Herein, the solution application method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

[0192] In addition to the above method, the organic light emitting device can also be manufactured by sequentially stacking a cathode material, an organic material layer, and an anode material on a substrate (International Publication No. 2003 / 012890). However, the manufacturing method is not limited thereto.

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

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

[0195] As the anode material, it is generally preferable to use a material having a large work function so as to smoothly inject holes into the organic material layer. Specific examples of the anode material usable in the present application include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0196] As the cathode material, it is generally preferable to use a material having a small work function so as to smoothly inject electrons into the organic material layer. 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 alloys thereof; multilayered structure materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0197] The hole injection material is a layer that injects holes from the electrode, and is preferably a compound having a capability of transporting holes, and thus has a role of injecting holes at the anode and an excellent role of injecting holes to the light emitting layer or light emitting material, prevents excitons generated from the light emitting layer from moving to the electron injection layer or electron injection material, and is excellent in forming a thin film. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic material, hexacenetetrabenzophenanthroline-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline, and polythiophene-based conductive polymer, but are not limited thereto.

[0198] The electron transport material is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer, and the hole transport material is suitably a material that can receive holes from the anode or hole injection layer to transfer holes to the light emitting layer, and has a large hole mobility. Specific examples thereof include arylamine-based organic material, conductive polymer, block copolymer in which a conjugated moiety exists together with a non-conjugated moiety, etc., but are not limited thereto.

[0199] The luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively, and cause the holes and electrons to combine to emit light in the visible light region, and is preferably a material with excellent quantum efficiency for fluorescence or phosphorescence. Specific examples include: 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; dipolystyrene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole and benzimidazole compounds; poly(p-styrene) (PPV) polymers; spirocyclic compounds; polyfluorene, lubrene, etc., but are not limited to these.

[0200] The luminescent layer may comprise a host material and a dopant material. Examples of host materials include condensed aromatic ring derivatives or heterocyclic compounds. In particular, examples of condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited to these examples.

[0201] Examples of dopant materials include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, and metal complexes. In particular, the aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted aryl amine groups, and examples include pyrene, anthracene, etc., having aryl amine groups. The styrene amine compound is a compound in which a substituted or unsubstituted aryl amine is substituted with at least one aryl vinyl group and one or more substituents selected from aryl, silyl, alkyl, and cycloalkyl groups, and the aryl amine group is substituted or unsubstituted. Specific examples include, but are not limited to, styrene amine, styrene diamine, styrene triamine, and styrene tetraamine. Furthermore, examples of the metal complex include, but are not limited to, iridium complexes and platinum complexes.

[0202] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that can effectively receive electrons from the cathode and transport them to the light-emitting layer, and is suitably a material with high electron mobility. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavonoid-metal complexes. The electron transport layer can be used with any desired cathode material, as used according to relevant techniques. In particular, examples of suitable cathode materials are conventional materials with low work functions, followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0203] The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound having the ability to transport electrons, has the effect of injecting electrons from a cathode and the excellent effect of injecting electrons into a light-emitting layer or a light-emitting material, prevents excitons generated from the light-emitting layer from moving to a hole injection layer, and is excellent in forming a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetra-carboxylic acid, fluorenylidene methane, anthrone and derivatives thereof, metal complexes, nitrogen-containing five-membered derivatives, and the like, but are not limited thereto.

[0204] Examples of the metal complex include lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinolate), zinc bis(10-hydroxybenzo[h]quinolate), chlorogallium bis(2-methyl-8-quinolate), gallium bis(2-methyl-8-quinolate)(o-cresol), aluminum bis(2-methyl-8-quinolate)(1-naphthol), gallium bis(2-methyl-8-quinolate)(2-naphthol), and the like, but are not limited thereto.

[0205] The organic light-emitting device according to the present application can be a top emission type, a bottom emission type, or a dual emission type, depending on the materials used.

[0206] In one exemplary embodiment of the present application, the compound of Formula 1 can be included in an organic solar cell or an organic transistor, in addition to the organic light-emitting device.

[0207] Invention Mode

[0208] The preparation of the compound represented by Formula 1 and the organic light-emitting device including the same will be specifically described in the following examples. However, the following examples are provided to illustrate the present application, and the scope of the present application is not limited thereto.

[0209] <Preparation Example>

[0210] <Preparation Example 1> Preparation of [Compound 1]

[0211] (10.0 g, 37.4 mmol) and 2-(2-(9,9-diphenyl-9H-fluoren-2-yl)phenyl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (19.4 g, 37.4 mmol) in 150 ml of THF. To this, 75 ml of 2.0 M K2CO3 and 0.8 g of Pd(PPh3)4 were put, and then the resulting mixture was stirred and refluxed for 5 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 1] (19.9 g, yield 85%, MS: [M+H + = 626).

[0212] <Preparation Example 2> Preparation of [Compound 2]

[0213] (10.0 g, 37.4 mmol) and 2-(2-(9,9-diphenyl-9H-fluoren-2-yl)phenyl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (19.4 g, 37.4 mmol) in 150 ml of THF. To this, 75 ml of 2.0 M K2CO3 and 0.8 g of Pd(PPh3)4 were put, and then the resulting mixture was stirred and refluxed for 5 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 1] (19.9 g, yield 85%, MS: [M+H + = 626).

[0214] <Preparation Example 3> Preparation of [Compound 3]

[0215] (10.0 g, 37.4 mmol) and 2-(2-(9,9-diphenyl-9H-fluoren-2-yl)phenyl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (19.4 g, 37.4 mmol) in 150 ml of THF. To this, 75 ml of 2.0 M K2CO3 and 0.8 g of Pd(PPh3)4 were put, and then the resulting mixture was stirred and refluxed for 5 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 1] (19.9 g, yield 85%, MS: [M+H + = 626).

[0216] <Preparation Example 4> Preparation of [Compound 5]

[0217] (10.0 g, 37.4 mmol) and 2-(3-(9,9-diphenyl-9H-fluoren-2-yl)phenyl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (19.4 g, 37.4 mmol) were put into 150 ml of THF. To this, 75 ml of 2.0 M K2CO3and 0.8 g of Pd(PPh3)4were put, and then the resulting mixture was stirred and refluxed for 7 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 5] (16.9 g, yield 72%, MS: [M+H + = 626)

[0218] <Preparation Example 5> Preparation of [Compound 7]

[0219] (10.0 g, 37.4 mmol) and 2-(3-(9,9-diphenyl-9H-fluoren-2-yl)phenyl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (19.4 g, 37.4 mmol) were put into 150 ml of THF. To this, 75 ml of 2.0 M K2CO3and 0.8 g of Pd(PPh3)4were put, and then the resulting mixture was stirred and refluxed for 7 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 5] (16.9 g, yield 72%, MS: [M+H + = 626)

[0220] <Preparation Example 6> Preparation of [Compound 13]

[0221] (10.0 g, 37.4 mmol) and 2-(3-(9,9-diphenyl-9H-fluoren-2-yl)phenyl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (19.4 g, 37.4 mmol) were put into 150 ml of THF. To this, 75 ml of 2.0 M K2CO3and 0.8 g of Pd(PPh3)4were put, and then the resulting mixture was stirred and refluxed for 7 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 5] (16.9 g, yield 72%, MS: [M+H + = 626)

[0222] <Preparation Example 7> Preparation of [Compound 27]

[0223] (10.0 g, 27.2 mmol) and 2-(4-(9,9-diphenyl-9H-fluoren-4-yl)phenyl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (14.7 g, 27.2 mmol) were put into 150 ml of THF. To this, 75 ml of 2.0 M K2CO3and 0.6 g of Pd(PPh3)4were put, and then the resulting mixture was stirred and refluxed for 6 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 27] (13.8 g, yield 70%, MS: [M+H] + = 726)

[0224] <Preparation Example 8> Preparation of [Compound 32]

[0225] (10.0 g, 27.2 mmol) and 2-(4-(9,9'-spirobi[fluoren]-4-yl)phenyl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (14.1 g, 27.2 mmol) were put into 150 ml of THF. To this, 75 ml of 2.0 M K2CO3and 0.6 g of Pd(PPh3)4were put, and then the resulting mixture was stirred and refluxed for 7 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 32] (15.0 g, yield 76%, MS: [M+H] + = 724)

[0226] <Preparation Example 9> Preparation of [Compound 36]

[0227] (10.0 g, 27.2 mmol) and 2-(4-(9,9-diphenyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (14.7 g, 27.2 mmol) were put into 150 ml of THF. To this, 75 ml of 2.0 M K2CO3and 0.6 g of Pd(PPh3)4were put, and then the resulting mixture was stirred and refluxed for 6 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 27] (13.8 g, yield 70%, MS: [M+H] + = 702)

[0228] <Preparation Example 10> Preparation of [Compound 46]

[0229] (10.0 g, 37.4 mmol) and 2-(4'-(9,9-diphenyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-4-yl)- 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (22.3 g, 37.4 mmol) were put into 150 ml of THF. To this, 75 ml of 2.0 M K2CO3 and 0.8 g of Pd(PPh3)4 were put, and then the resulting mixture was stirred and refluxed for 6 hours.

[0230] The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 46] (17.9 g, yield 68%, MS: [M+H] = 702). + = 702)

[0231] Preparation Example 11: Preparation of [Compound 47]

[0232] (10.0 g, 37.4 mmol) and 2-(4'-(9,9'-spirobi[fluoren]-2-yl)-[1,1'-biphenyl]-4-yl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (22.2 g, 37.4 mmol) were put into 150 ml of THF. To this, 75 ml of 2.0 M K2CO3 and 0.8 g of Pd(PPh3)4 were put, and then the resulting mixture was stirred and refluxed for 8 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 47] (21.2 g, yield 81%, MS: [M+H] = 700). + = 700)

[0233] Preparation Example 12: Preparation of [Compound 67]

[0234] (10.0 g, 37.4 mmol) and 2-(4'-(9,9-diphenyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-4-yl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (22.3 g, 37.4 mmol) were put into 150 ml of THF. To this, 75 ml of 2.0 M K2CO3 and 0.8 g of Pd(PPh3)4 were put, and then the resulting mixture was stirred and refluxed for 8 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [Compound 67] (18.6 g, yield 71%, MS: [M+H] = 702). + = 702)

[0235] <Preparation Example 13> Preparation of [Compound 80]

[0236] 2-Chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (10.0 g, 36.0 mmol) and 2-(4-(9,9-diphenyl-9H-fluorene-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxane-pentaborane (18.7 g, 36.0 mmol) were placed in 150 mL of THF. 75 mL of 2.0 M K₂CO₃ and 0.8 g of Pd(PPh₃)₄ were added, and the resulting mixture was stirred and refluxed for 6 hours. The mixture was cooled to room temperature, and the solid obtained by filtration was recrystallized from the mixture using chloroform and ethanol to prepare [Compound 80]. (16.0 g, 70% yield, MS: [M+H]) + =636)

[0237] <Example>

[0238] [Example 1]

[0239] A thin coating of indium tin oxide (ITO) is applied until it has... A thick glass substrate was immersed in distilled water containing a cleaning agent and ultrasonically cleaned. In this case, a product manufactured by Fischer Co. was used as the detergent, and the distilled water was filtered twice using a filter manufactured by Millipore Co. After cleaning the ITO for 30 minutes, it was ultrasonically cleaned twice for 10 minutes each time with distilled water. Following the washing with distilled water, the substrate was ultrasonically cleaned using isopropanol, acetone, and methanol solvents, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes and then transferred to a vacuum evaporator.

[0240] The following compound [HI-A] was thermally vacuum deposited onto a transparent ITO electrode prepared as described above. The thickness of the compound [HAT] is increased to form a hole injection layer. And the following compound [HT-A] Sequential vacuum deposition is performed on the hole injection layer to form a hole transport layer.

[0241] Subsequently, the following compounds [BH] and [BD] were vacuum deposited on the hole transport layer at a weight ratio of 25:1 to form a layer with... The film thickness is adjusted to form a light-emitting layer.

[0242] Compound 1 and the following compound [LiQ] (lithium quinoline) were vacuum deposited on the light-emitting layer in a 1:1 weight ratio to form a light-emitting layer with... thickness of 1 nm and 100 nm, respectively, thereby forming a cathode. and of 1 nm and 100 nm, respectively.

[0243] In the above step, the deposition rate of the organic material is maintained at the deposition rate of lithium fluoride and aluminum of the cathode is maintained at and and the degree of vacuum during deposition is maintained at 1 x 10 -7 to 5 x 10 -8 torr, thereby manufacturing an organic light emitting device.

[0244]

[0245] [Example 2]

[0246] An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 2] was used instead of [Compound 1] of [Example 1].

[0247] [Example 3]

[0248] An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 3] was used instead of [Compound 1] of [Example 1].

[0249] [Example 4]

[0250] An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 5] was used instead of [Compound 1] of [Example 1].

[0251] [Example 5]

[0252] An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 7] was used instead of [Compound 1] of [Example 1].

[0253] [Example 6]

[0254] An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 13] was used instead of [Compound 1] of [Example 1].

[0255] [Example 7]

[0256] An organic light emitting device was manufactured in the same manner as in [Example 1], except that [Compound 27] was used instead of [Compound 1] of [Example 1].

[0257] [Example 8]

[0258] An organic light-emitting device was produced in the same manner as in [Example 1], except that [Compound 32] was used instead of [Compound 1] of [Example 1].

[0259] [Example 9]

[0260] An organic light-emitting device was produced in the same manner as in [Example 1], except that [Compound 36] was used instead of [Compound 1] of [Example 1].

[0261] [Example 10]

[0262] An organic light-emitting device was produced in the same manner as in [Example 1], except that [Compound 46] was used instead of [Compound 1] of [Example 1].

[0263] [Example 11]

[0264] An organic light-emitting device was produced in the same manner as in [Example 1], except that [Compound 47] was used instead of [Compound 1] of [Example 1].

[0265] [Example 12]

[0266] An organic light-emitting device was produced in the same manner as in [Example 1], except that [Compound 67] was used instead of [Compound 1] of [Example 1].

[0267] [Example 13]

[0268] An organic light-emitting device was produced in the same manner as in [Example 1], except that [Compound 80] was used instead of [Compound 1] of [Example 1].

[0269] [Comparative Example 1]

[0270] An organic light-emitting device was produced in the same manner as in [Example 1], except that [ET-A] was used instead of [Compound 1] of [Example 1].

[0271] [Comparative Example 2]

[0272] An organic light-emitting device was produced in the same manner as in [Example 1], except that [ET-B] was used instead of [Compound 1] of [Example 1].

[0273] For the organic light-emitting device produced by the above method, the driving voltage and luminous efficiency were measured at a current density of 10 mA / cm 2 , and the time (T 90 ) to reach 90% of the initial luminance was measured at a current density of 20 mA / cm 2 . The results are shown in Table 1 below.

[0274] [Table 1]

[0275]

[0276] According to the results of the table, the compound represented by Formula 1 according to the present application can be used for the organic layer capable of simultaneously injecting and transporting electrons of the organic light emitting device. The organic light emitting device using the same has a low driving voltage and high efficiency, and the stability of the device can be improved by the hole stability of the compound.

[0277] In particular, the compound represented by Formula 1 according to the present application is excellent in terms of thermal stability, and can be used in a mixture with an n-type dopant when used for the organic layer capable of simultaneously injecting and transporting electrons.

[0278] Further, according to one exemplary embodiment of the present application, the case where the compound represented by Formula 8 is used for the organic light emitting device has a lower driving voltage and / or higher efficiency compared to the case where the compound represented by Formula 5 to Formula 7 is used for the organic light emitting device, and the stability of the device can be increased by the hole stability of the compound.

[0279] [Explanation of Reference Numerals]

[0280] 1: Substrate

[0281] 2: Anode

[0282] 3: Light emitting layer

[0283] 4: Cathode

[0284] 5: Hole injection layer

[0285] 6: Hole transport layer

[0286] 7: Light emitting layer

[0287] 8: Electron transport layer

[0288] The present application also provides the following technical solutions:

[0289] Note 1. A compound represented by the following Formula 1:

[0290] [Formula 1]

[0291]

[0292] In Formula 1,

[0293] Ar1and Ar2are the same as each other, and are phenyl, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl(sulfinyl) group, an aryl(sulfinyl) group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group; a biphenyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl(sulfinyl) group, an aryl(sulfinyl) group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group; a naphthyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl(sulfinyl) group, an aryl(sulfinyl) group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group; or a phenanthryl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl(sulfinyl) group, an aryl(sulfinyl) group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group;

[0294] L is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

[0295] R1and R2are the same or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkyl(ene)sulfonyl group; a substituted or unsubstituted aryl(ene)sulfonyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted aralkenyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted alkylamino group; a substituted or unsubstituted aralkylamino group; a substituted or unsubstituted heteroarylaminogroup; a substituted or unsubstituted arylamino group; a substituted or unsubstituted arylheteroarylamino group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or optionally form a substituted or unsubstituted ring together with an adjacent group,

[0296] R3and R4are the same or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkyl(ene)sulfonyl group; a substituted or unsubstituted aryl(ene)sulfonyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted aralkenyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted alkylamino group; a substituted or unsubstituted aralkylamino group; a substituted or unsubstituted arylphosphine group; or a substituted or unsubstituted phosphine oxide group; or optionally form a substituted or unsubstituted ring together with an adjacent group,

[0297] m is an integer of 1 to 5,

[0298] a is an integer of 0 to 3, and

[0299] b is an integer of 0 to 4, and

[0300] when m, a, and b are each 2 or more, the structures in the parentheses are the same or different from each other.

[0301] Note 2. The compound according to Note 1, wherein Formula 1 is represented by any one of the following Formulae 2 to 4:

[0302] [Formula 2]

[0303]

[0304] [Formula 3]

[0305]

[0306] [Formula 4]

[0307]

[0308] In Formulae 2 to 4,

[0309] Ar1, Ar2, L, R3, R4, a, b, and m are the same as defined in Formula 1,

[0310] R11, R12, R21, and R22 are the same as defined for R3 and R4,

[0311] X1and X2are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkyl(ene)sulfinyl group; a substituted or unsubstituted aryl(ene)sulfinyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted aralkenyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamine group; a substituted or unsubstituted arylphosphine group; or a substituted or unsubstituted phosphine oxide group; or optionally forms, together with an adjacent group, a substituted or unsubstituted ring,

[0312] r11and r12are the same as or different from each other, and are each independently an integer of 0 to 5,

[0313] r21and r22are the same as or different from each other, and are each independently an integer of 0 to 4, and

[0314] When r11, r12, r21, and r22are each 2 or more, the structures in parentheses are the same as or different from each other.

[0315] Note 3. The compound according to Note 1, wherein Formula 1 is represented by any one of the following Formulae 5 to 8:

[0316] [Formula 5]

[0317]

[0318] [Formula 6]

[0319]

[0320] [Formula 7]

[0321]

[0322] [Formula 8]

[0323]

[0324] In Formula 5 to Formula 8,

[0325] Ar1, Ar2, L, R1to R4, m, a, and b are defined the same as defined in Formula 1.

[0326] Note 4. The compound according to Note 1, wherein L is selected from any one of the following structures:

[0327]

[0328]

[0329] the structure is optionally unsubstituted or substituted with one or more substituents selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkyl(sulfinyl) group; an aryl(sulfinyl) group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an aryl phosphine group; and a heterocyclic group.

[0330] Note 5. The compound according to Note 1, wherein L is a phenylene group or a biphenylene group.

[0331] Note 6. The compound according to Note 1, wherein Ar1and Ar2are the same as each other, and are a phenyl group, which is unsubstituted or substituted with one or more substituents selected from deuterium and an alkyl group; a biphenyl group, which is unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group, and an aryl group; a naphthyl group, which is unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group, and an aryl group; or a phenanthryl group, which is unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group, and an aryl group.

[0332] Note 7. The compound according to Note 1, wherein R1and R2are the same or different from each other, and each independently alkyl; or aryl, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, alkyl, and alkoxy; or combine with each other to form a ring.

[0333] Note 8. The compound according to Note 1, wherein R3and R4are hydrogen.

[0334] Note 9. The compound according to Note 1, wherein moieties are selected from any one of the following structures:

[0335]

[0336]

[0337] In the structures,

[0338] R1and R2are the same as defined in Formula 1, and

[0339] the structures can be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthio group; arylthio group; alkyl(thio) sulfinyl group; aryl(thio) sulfinyl group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkylamine group; heteroarylamine group; arylamine group; aryl phosphine group; and heterocyclic group.

[0340] Note 10. The compound according to Note 1, wherein the compound of Formula 1 is selected from any one of the following compounds:

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351] Note 11. An organic light-emitting device comprising:

[0352] a first electrode;

[0353] a second electrode disposed to face the first electrode; and

[0354] one or more layers of an organic material disposed between the first electrode and the second electrode,

[0355] wherein one or more of the layers of the organic material comprises the compound according to any one of Notes 1 to 10.

[0356] Note 12. The organic light-emitting device according to Note 11, wherein the layer of the organic material comprising the compound is a hole-injection layer, a hole-transport layer, or a layer that injects and transports holes simultaneously.

[0357] Note 13. The organic light-emitting device according to Note 11, wherein the layer of the organic material comprising the compound is an electron-injection layer, an electron-transport layer, or a layer that injects and transports electrons simultaneously.

[0358] Note 14. The organic light-emitting device according to Note 11, wherein the layer of the organic material comprising the compound is an emission layer.

Claims

1. An organic light-emitting device comprising: a first electrode; a second electrode disposed to face the first electrode; and one or more layers of an organic material disposed between the first electrode and the second electrode, wherein one or more of the layers of the organic material comprises a compound which is a compound represented by the following formula 6, and wherein the layer of the organic material comprising the compound is an electron injection layer, an electron transport layer, or a layer which injects and transports electrons simultaneously: [Formula 6] In formula 6, Ar1and Ar2are the same as each other, and are a phenyl group or a biphenyl group; R1and R2are a methyl group, L is R3and R4are hydrogen, m is 1, a is an integer of 0 to 3, and b is an integer of 0 to 4.

2. The organic light-emitting device according to claim 1, wherein the compound of formula 6 is any one selected from the following compounds: ​

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