Compound and organic electronic device comprising the same

Abstract

The present specification provides a compound of Formula 1 and an organic electronic device comprising the same.

Description

Technology Field

[0001] This specification relates to compounds and organic electronic devices containing the same. Background Technology

[0002] A representative example of an organic electronic device is the organic light-emitting diode (OLED). Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes that utilize this phenomenon typically have a structure containing an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for instance, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall back to the ground state.

[0003] The materials used in organic light-emitting diodes are mostly pure organic materials or complex compounds in which organic materials and metals form a complex. Depending on their application, the materials used in the organic light-emitting diodes can be classified into hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials. Here, organic materials with p-type properties, that is, organic materials that oxidize easily and maintain an electrochemically stable state upon oxidation, are mainly used as hole injection materials or hole transport materials. Meanwhile, organic materials with n-type properties, that is, organic materials that reduce easily and maintain an electrochemically stable state upon reduction, are mainly used as electron injection materials or electron transport materials. For the light-emitting layer material, it is preferable to have a material that possesses both p-type and n-type properties simultaneously, that is, a material that maintains a stable form in both oxidation and reduction states, and it is preferable to have a material with high luminous efficiency that converts excitons into light when they are formed.

[0004] In order to fully exhibit the excellent characteristics of the aforementioned organic light-emitting diode, the development of materials forming the organic layer within the device is continuously required. Prior art literature

[0005] Republic of Korea Patent Application No. 10-2015-0172417 (Filed Dec. 4, 2015) The problem to be solved

[0006] This specification relates to compounds and organic electronic devices containing the same. means of solving the problem

[0007] One embodiment of the present specification provides a compound of the following chemical formula 1.

[0008] [Chemical Formula 1]

[0009]

[0010] In the above chemical formula 1,

[0011] A is represented by the following chemical formula 2 or 3, and

[0012] [Chemical Formula 2]

[0013]

[0014] [Chemical Formula 3]

[0015]

[0016] In the above chemical formulas 1 to 3,

[0017] R1 to R20 are the same or different from each other, and each independently represents hydrogen; deuterium; or the following chemical formula 4, and

[0018] When the above A is represented by Chemical Formula 2, at least one of the above R1 to R12 is represented by the following Chemical Formula 4, and

[0019] When the above A is represented by Chemical Formula 3, at least one of the above R1 to R6 and R13 to R20 is represented by the following Chemical Formula 4, and

[0020] [Chemical Formula 4]

[0021]

[0022] In the above chemical formula 4,

[0023] L is a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkenylene group; or a substituted or unsubstituted heteroarylene group comprising one or more atoms of O, N, S and P as heteroelements, and

[0024] X is deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group comprising one or more atoms of N, O, S, and P as heteroelements, and

[0025] m is an integer from 0 to 4, and

[0026] The dotted lines of the above chemical formulas 2 and 3 represent the regions that combine with chemical formula 1, and

[0027] Where the above L is a direct bond, the above X is a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group comprising one or more atoms of N, O, S, and P as heteroelements, and

[0028] If either of the above R14 and R19 is represented by the above chemical formula 4, the remainder of the above R14 and R19 is hydrogen, and

[0029] Where A is represented by Chemical Formula 3 and R3 is represented by Chemical Formula 4, at least one of R1, R2, R4, R5, R6 and R13 to R20 is represented by Chemical Formula 4, and

[0030] When A is represented by Chemical Formula 3 and R4 is represented by Chemical Formula 4, at least one of R1, R2, R3, R5, R6 and R13 to R20 is represented by Chemical Formula 4.

[0031] In addition, one embodiment of the present specification provides an organic electronic device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein the one or more organic layers comprise the compound. Effects of the invention

[0032] The compounds described in this specification can be used as materials for the organic layer of an organic electronic device. When an organic electronic device comprising a compound according to at least one embodiment is manufactured, an organic electronic device having a low driving voltage and a long lifespan can be obtained.

[0033] In particular, when the compound of the present invention is used in a layer that simultaneously performs electron transport and electron injection, a hole blocking layer, and an emissive layer, the driving voltage of the device is lowered, and the efficiency of the device is increased and the lifespan is extended. Brief explanation of the drawing

[0034] FIG. 1 illustrates an example of an organic electronic device comprising a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). FIG. 2 illustrates an example of an organic electronic device comprising a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (7), a layer (8) that simultaneously transports and injects electrons, and a cathode (4). FIG. 3 illustrates an example of an organic electronic device comprising a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (7), a hole blocking layer (9), a layer (8) that simultaneously transports and injects electrons, and a cathode (4). Specific details for implementing the invention

[0035] The present specification will be described in more detail below.

[0036] The present specification provides a compound of the following chemical formula 1. When the compound of the following chemical formula 1 is included in the organic layer of an organic electronic device, the driving voltage of the device is lowered, and the efficiency of the device is increased and the lifespan is extended.

[0037] [Chemical Formula 1]

[0038]

[0039] In the above chemical formula 1,

[0040] A is represented by the following chemical formula 2 or 3, and

[0041] [Chemical Formula 2]

[0042]

[0043] [Chemical Formula 3]

[0044]

[0045] In the above chemical formulas 1 to 3,

[0046] R1 to R20 are the same or different from each other, and each independently represents hydrogen; deuterium; or the following chemical formula 4, and

[0047] When the above A is represented by Chemical Formula 2, at least one of the above R1 to R12 is represented by the following Chemical Formula 4, and

[0048] When the above A is represented by Chemical Formula 3, at least one of the above R1 to R6 and R13 to R20 is represented by the following Chemical Formula 4, and

[0049] [Chemical Formula 4]

[0050]

[0051] In the above chemical formula 4,

[0052] L is a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkenylene group; or a substituted or unsubstituted heteroarylene group comprising one or more atoms of O, N, S and P as heteroelements, and

[0053] X is deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group comprising one or more atoms of N, O, S, and P as heteroelements, and

[0054] m is an integer from 0 to 4, and

[0055] The dotted lines of the above chemical formulas 2 and 3 represent the regions that combine with chemical formula 1, and

[0056] Where the above L is a direct bond, the above X is a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group comprising one or more atoms of N, O, S, and P as heteroelements, and

[0057] If either of the above R14 and R19 is represented by the above chemical formula 4, the remainder of the above R14 and R19 is hydrogen, and

[0058] Where A is represented by Chemical Formula 3 and R3 is represented by Chemical Formula 4, at least one of R1, R2, R4, R5, R6 and R13 to R20 is represented by Chemical Formula 4, and

[0059] When A is represented by Chemical Formula 3 and R4 is represented by Chemical Formula 4, at least one of R1, R2, R3, R5, R6 and R13 to R20 is represented by Chemical Formula 4.

[0060] In this specification, when it is stated that a component is located "on" another component, this includes not only cases where a component is in contact with another component, but also cases where another component exists between the two components.

[0061] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0062] Throughout this specification, the term “combination thereof” included in the Markush-type expression means one or more mixtures or combinations selected from the group consisting of the components described in the Markush-type expression, and means including one or more selected from the group consisting of said components.

[0063] The substituents of this specification are described in detail below, but are not limited thereto.

[0064] In this specification, means a site that is bonded to another substituent or bonding site.

[0065] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0066] In this specification, the term “substituted or unsubstituted” means being substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium (-D); halogen group; nitrile group; nitro group; alkyl group; alkenyl group; cycloalkyl group; alkoxy group; amine group; silyl group; aryl group; and heteroaryl group, being substituted with two or more of the exemplified substituents connected to a substituent, or having no substituents at all.

[0067] In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0068] In the present specification, the alkyl group may be a straight chain, a branched chain, or a cyclic chain, and the number of carbon atoms is not particularly limited but is preferably 1 to 50. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 40. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of alkyl groups 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, Examples include 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, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0069] In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the 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-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited thereto.

[0070] In the present specification, the alkynyl group may be a straight chain or a non-straight chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include alkynyl groups such as ethinyl, propynyl, 2-methyl-2-propynyl, 2-butynyl, and 2-fenthynyl, but are not limited thereto.

[0071] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, 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 group, etc. are used, but are not limited thereto.

[0072] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 1 to 40 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.

[0073] Substituents comprising alkyl groups, alkoxy groups and other alkyl groups described in this specification include both straight-chain and broken-chain forms.

[0074] In this specification, the amine group may be selected from the group consisting of -NH2; monoalkylamine group; dialkylamine group; N-alkylarylamine group; monoarylamine group; diarylamine group; triarylamine group; N-arylheteroarylamine group; N-alkylheteroarylamine group, monoheteroarylamine group, and diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group, dimethylamine group, trimethylamine group, ethylamine group, diethylamine group, triethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc., are included but are not limited thereto.

[0075] In this specification, the silyl group is -SiY a Y b Y cIt can be represented by the chemical formula of, and the above Y a , Y b and Y c Each may be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specifically, the silyl group includes, but is not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0076] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quadrphenyl group, etc., but is not limited thereto. As a polycyclic aryl group, the aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto.

[0077] In the present specification, the fluorenyl group may be substituted, and two substituents may combine to form a spiro structure.

[0078] When the above fluorenyl group is substituted, (spirofluorenyl group), (spirobifluorenyl group), (9,9-dimethylfluorenyl group) and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group), but is not limited thereto.

[0079] 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 examples described above.

[0080] In this specification, the heteroaryl group is an aromatic ring comprising one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may comprise one or more atoms selected from the group consisting of O, N, P, Se, and S. The number of carbon atoms is not particularly limited, but it is preferred to have 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms in the heteroaryl group is 2 to 30. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include, but are not limited to, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, pyridine, pyrimidine, triazine, triazole, quinolinyl, quinazolin, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophen, dibenzothiophen, benzofuran, phenanthroline, isooxazole, thiadiazole, naphthobenzofuran, and dibenzofuran.

[0081] In this specification, an arylene group refers to a group having two binding sites to an aryl group, i.e., a divalent group. Except for the fact that each of these is a divalent group, the description of the aryl group described above may apply.

[0082] In this specification, a heteroarylene group refers to a heteroaryl group having two binding sites, i.e., a divalent group. Except for the fact that each of these is a divalent group, the description of the heteroaryl group described above may apply.

[0083] In this specification, "adjacent" groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the atom on which the substituent is substituted, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

[0084] In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, "ring" means a hydrocarbon ring; or a heteroring.

[0085] The above hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the above cycloalkyl or aryl groups, except for the above divalent group.

[0086] Except for the fact that the above heterocyclic ring is divalent, the description of the above heteroaryl group may be applied.

[0087] In one embodiment of the present specification, the formula 1 may be any one of the following formulas 5 and 6.

[0088] [Chemical Formula 5]

[0089]

[0090] [Chemical Formula 6]

[0091]

[0092] In the above chemical formulas 5 and 6, R1 to R20 are as defined in the above chemical formulas 1 to 3.

[0093] In one embodiment of the present specification, A may be represented by Chemical Formula 2.

[0094] In one embodiment of the present specification, when A is represented by Chemical Formula 2, at least one of R1 to R12 may be represented by Chemical Formula 4.

[0095] In one embodiment of the present specification, when A is represented by Formula 2, at least one of R7 to R12 may be represented by Formula 4.

[0096] In one embodiment of the present specification, A may be represented by Chemical Formula 3.

[0097] In one embodiment of the present specification, when A is represented by Chemical Formula 3, at least one of R1 to R6 and R13 to R20 may be represented by Chemical Formula 4.

[0098] In one embodiment of the present specification, when A is represented by Chemical Formula 3, at least one of R1, R2, R5, R6 and R13 to R20 may be represented by Chemical Formula 4.

[0099] In one embodiment of the present specification, when A is represented by Chemical Formula 3, at least one of R13 to R20 may be represented by Chemical Formula 4.

[0100] In one embodiment of the present specification, the formula 1 may be the formula 5.

[0101] In one embodiment of the present specification, the formula 1 may be the formula 6.

[0102] In one embodiment of the present specification, R1 to R20 may be the same or different from each other and may each independently represent hydrogen; or the formula 4.

[0103] In one embodiment of the present specification, R1 to R6 are all hydrogen.

[0104] In one embodiment of the present specification, at least one of R1 to R6 may be represented by Formula 4.

[0105] In one embodiment of the present specification, at least one of R1 to R12 may be represented by Formula 4.

[0106] In one embodiment of the present specification, at least one of R7 to R12 may be represented by Formula 4.

[0107] In one embodiment of the present specification, when A is represented by Chemical Formula 2, R3 and R10 are represented by Chemical Formula 4, and R1, R2, R4 to R9, R11 and R12 are hydrogen.

[0108] In one embodiment of the present specification, at least one of R1, R2, R5, R6 and R13 to R20 may be represented by Chemical Formula 4.

[0109] In one embodiment of the present specification, at least one of R13 to R20 may be represented by Chemical Formula 4.

[0110] In one embodiment of the present specification, when A is represented by Chemical Formula 3, at least one of R1 to R6 and R13 to R20 is represented by Chemical Formula 4, and the remainder of R1, R2, R5, R6 and R13 to R20 is hydrogen.

[0111] In one embodiment of the present specification, where A is represented by Chemical Formula 3 and R3 is represented by Chemical Formula 4, at least one of R1, R2, R4, R5, R6 and R13 to R20 is represented by Chemical Formula 4.

[0112] In one embodiment of the present specification, where A is represented by Chemical Formula 3 and R4 is represented by Chemical Formula 4, at least one of R1, R2, R3, R5, R6 and R13 to R20 is represented by Chemical Formula 4.

[0113] In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group comprising one or more atoms of O, N, S and P as heteroelements.

[0114] In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a heteroarylene group having 2 to 60 carbon atoms comprising one or more atoms of O, N, S and P as heteroelements.

[0115] In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a heteroarylene group having 2 to 30 carbon atoms comprising one or more atoms of O, N, S and P as heteroelements.

[0116] In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted anthracenylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted pyridinylene group; a substituted or unsubstituted pyrimidinylene group; a substituted or unsubstituted triazinylene group; a substituted or unsubstituted thiophenylene group; a substituted or unsubstituted furanilene group; a substituted or unsubstituted dibenzothiophenylene group; a substituted or unsubstituted dibenzofuranylene group; or a substituted or unsubstituted carbazolilene group.

[0117] In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a fluorenylene group substituted or unsubstituted with an alkyl group; a substituted or unsubstituted pyridinylene group; a substituted or unsubstituted triazinylene group; a substituted or unsubstituted thiophenylene group; a substituted or unsubstituted furanilene group; a substituted or unsubstituted dibenzothiophenylene group; a substituted or unsubstituted dibenzofuranilene group; or a substituted or unsubstituted carbazolilene group.

[0118] In one embodiment of the present specification, L is a direct bond; a phenylene group; a biphenylene group; a naphthylene group; a dimethylfluorenylene group; a pyridinylene group; a triazinylene group substituted or unsubstituted with a phenyl group; a thiophenylene group; a furanilene group; a dibenzothiophenylene group; a dibenzofuranilene group; or a carbazolilene group substituted or unsubstituted with a phenyl group.

[0119] In one embodiment of the present specification, X is deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms; a substituted or unsubstituted amine group; 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 comprising one or more atoms of N, O, S and P as heteroatoms.

[0120] In one embodiment of the present specification, X is deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; a substituted or unsubstituted amine 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 comprising one or more atoms selected from N, O, S, and P as heteroatoms.

[0121] In one embodiment of the present specification, X is deuterium; a nitrile group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; a substituted or unsubstituted amine 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 comprising one or more atoms selected from N, O, S, and P as heteroatoms.

[0122] In one embodiment of the present specification, X is deuterium; a nitrile group; an amine group substituted or unsubstituted with an aryl 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 fluorenyl group; a substituted or unsubstituted triazine group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

[0123] In one embodiment of the present specification, X is deuterium; a nitrile group; an amine group substituted or unsubstituted with a phenyl group; a phenyl group substituted or unsubstituted with a deuterium, aryl group, or heteroaryl group; a biphenyl group substituted or unsubstituted with a nitrile group or an aryl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group substituted with an alkyl group; a substituted or unsubstituted triazine group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

[0124] In one embodiment of the present specification, X is deuterium; a nitrile group; an amine group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms; a phenyl group substituted or unsubstituted with a deuterium, a nitrile group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group; a biphenyl group substituted or unsubstituted with a nitrile group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group; a terphenyl group; a naphthyl group substituted or unsubstituted with a nitrile group, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a dibenzofuranyl group; a carbazolyl group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms; a dimethylfluorenyl group; a benzocarbazolyl group; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a triazine group substituted or unsubstituted with a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0125] In one embodiment of the present specification, X is deuterium; a nitrile group; a diphenylamine group; a phenyl group substituted or unsubstituted with a deuterium, a nitrile group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; a biphenyl group substituted or unsubstituted with a nitrile group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; a terphenyl group; a naphthyl group substituted or unsubstituted with a nitrile group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group or a substituted or unsubstituted naphthyl group; a dibenzofuranyl group; a carbazolyl group substituted or unsubstituted with a phenyl group; a dimethylfluorenyl group; a benzocarbazolyl group; It is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a terphenyl group, a phenanthrene group, a substituted or unsubstituted naphthyl group, a phenalene group, a fluoranthene group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, or a triazine group substituted with a pyridine group.

[0126] In one embodiment of the present specification, where L is a direct bond, X is deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 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 comprising one or more atoms of N, O, S and P as heteroatoms.

[0127] In one embodiment of the present specification, where L is a direct bond, X is deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; 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 comprising one or more atoms of N, O, S and P as heteroatoms.

[0128] In one embodiment of the present specification, where L is a direct bond, X is deuterium; a nitrile group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; 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 comprising one or more atoms of N, O, S and P as heteroelements.

[0129] In one embodiment of the present specification, where L is a direct bond, X is deuterium; a nitrile 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 fluorenyl group; a substituted or unsubstituted triazine group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

[0130] In one embodiment of the present specification, where L is a direct bond, X is deuterium; a nitrile group; a phenyl group substituted or unsubstituted with a deuterium, aryl group or heteroaryl group; a biphenyl group substituted or unsubstituted with a nitrile group or aryl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group substituted with an alkyl group; a substituted or unsubstituted triazine group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

[0131] In one embodiment of the present specification, where L is a direct bond, X is a deuterium; a nitrile group; a phenyl group substituted or unsubstituted with a deuterium, a nitrile group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; a biphenyl group substituted or unsubstituted with a nitrile group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; a terphenyl group; a naphthyl group substituted or unsubstituted with a nitrile group, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a dibenzofuranyl group; a carbazolyl group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms; a dimethylfluorenyl group; a benzocarbazolyl group; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a triazine group substituted or unsubstituted with a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0132] In one embodiment of the present specification, where L is a direct bond, X is deuterium; a nitrile group; a phenyl group substituted or unsubstituted with a deuterium, a nitrile group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; a biphenyl group substituted or unsubstituted with a nitrile group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; a terphenyl group; a naphthyl group substituted or unsubstituted with a nitrile group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted terphenyl group or a substituted or unsubstituted naphthyl group; a dibenzofuranyl group; a carbazolyl group substituted or unsubstituted with a phenyl group; a dimethylfluorenyl group; a benzocarbazolyl group; It is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a terphenyl group, a phenanthrene group, a substituted or unsubstituted naphthyl group, a phenalene group, a fluoranthene group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, or a triazine group substituted with a pyridine group.

[0133] In one embodiment of the present specification, m is an integer from 0 to 3.

[0134] In one embodiment of the present specification, m is an integer from 0 to 2.

[0135] In one embodiment of the present specification, m is 0 or 1.

[0136] In one embodiment of the present specification, m is 1.

[0137] In one embodiment of the present specification, m is 0.

[0138] In one embodiment of the present specification, the fact that m is 0 means that the connector inside the parentheses is a direct connection.

[0139] In one embodiment of the present specification, the compound of Formula 1 may be represented by any one of the following compounds.

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239] The compound of Formula 1 of this specification may have a core structure prepared as shown in the following reaction scheme. Substituents may be bonded by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.

[0240] <Reaction Equation 1>

[0241]

[0242] Naphthalene-1,8-diamine and IM1 were heated under reflux with acetic acid and acetonitrile mixed in appropriate proportions. During the reaction, solid P1-A precipitated, and after the reaction was completed, the mixture was cooled and filtered. The light brown product P1 was obtained by washing with a mixed solvent of acetic acid and acetonitrile and hexane. The method for producing P1 from P1-A is described in Preparation Example 1-1 below.

[0243] <Reaction Equation 2>

[0244]

[0245] Naphthalene-1,8-diamine and IM2 were heated under reflux with acetic acid and acetonitrile mixed in appropriate proportions. During the reaction, solid P2-A precipitated, and after the reaction was completed, the mixture was cooled and filtered. The light brown product P2 was obtained by washing with a mixed solvent of acetic acid and acetonitrile and hexane. The method for producing P2 from P2-A was carried out in the same manner as in Preparation Example 1-1 described below, except that P2-A was used instead of P1-A.

[0246] In this specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can also be controlled by introducing various substituents into the core structure of the above structure.

[0247] In addition, by introducing various substituents into a core structure having the above-described structure, compounds possessing the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents primarily used in hole injection layer materials, hole transport materials, electron transport materials, electron suppression materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting diodes into the core structure, materials that satisfy the conditions required for each organic layer can be synthesized.

[0248] In addition, the organic electronic device according to the present specification comprises a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound represented by the aforementioned chemical formula 1.

[0249] The organic electronic device of the present specification can be manufactured by conventional methods and materials for manufacturing organic electronic devices, except for forming one or more organic layers using the aforementioned compounds.

[0250] In one embodiment of the present invention, the organic electronic device may be selected from the group consisting of an organic light-emitting device, an organic phosphorescent device, an organic solar cell, an organic photosensitive material (OPC), and a glass transistor.

[0251] The following provides examples of organic light-emitting diodes.

[0252] The above compound can be formed as an organic layer by vacuum deposition as well as by solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0253] The organic layer of the organic light-emitting device of the present specification may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present specification may have a structure comprising, as an organic layer, a hole injection layer, a hole transport layer, a layer that performs hole transport and hole injection simultaneously, an electron blocking layer, an emitting layer, an electron transport layer and an electron injection layer, a layer that performs electron transport and electron injection simultaneously, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller or larger number of organic layers.

[0254] In the organic light-emitting device of the present specification, the organic layer may include a layer that simultaneously performs electron transport and electron injection, and the layer that simultaneously performs electron transport and electron injection may include the aforementioned compound.

[0255] In the organic light-emitting device of the present specification, the organic layer may include a hole-blocking layer, and the hole-blocking layer may include the aforementioned compound.

[0256] In the organic light-emitting device of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound described above.

[0257] According to another embodiment, the organic layer comprises a light-emitting layer, and the light-emitting layer may include the aforementioned compound as a dopant of the light-emitting layer.

[0258] In another embodiment, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the aforementioned compound as a dopant of the light-emitting layer and may further comprise a host.

[0259] In another embodiment, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the aforementioned compound as a dopant of the light-emitting layer, comprises a fluorescent host or a phosphorescent host, and may comprise other organic compounds, metals, or metal compounds as dopants.

[0260] As another example, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the aforementioned compound as a dopant of the light-emitting layer, and comprises a fluorescent host or a phosphorescent host, and can be used together with an iridium-based (Ir) dopant.

[0261] According to another embodiment, the organic layer comprises a light-emitting layer, and the light-emitting layer may include the aforementioned compound as a host of the light-emitting layer.

[0262] As another example, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the aforementioned compound as a host of the light-emitting layer and may further comprise a dopant.

[0263] As another example, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the aforementioned compound as a host of the light-emitting layer and may further comprise a dopant. The content of the dopant may be 1 to 20 parts by weight per 100 parts by weight of the host, and more preferably 1 to 5 parts by weight.

[0264] In the organic light-emitting device of the present specification, the organic layer comprises an electronic blocking layer, and the electronic blocking layer may comprise the aforementioned compound.

[0265] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0266] According to another embodiment, the first electrode is a negative electrode and the second electrode is a positive electrode.

[0267] The above organic light-emitting device may have a stacked structure such as, for example, the following, but is not limited thereto.

[0268] (1) Anode / hole transport layer / emissive layer / cathode

[0269] (2) Anode / hole injection layer / hole transport layer / emissive layer / cathode

[0270] (3) Anode / hole transport layer / emissive layer / electron transport layer / cathode

[0271] (4) Anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0272] (5) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / cathode

[0273] (6) Anode / hole injection layer / hole transport layer / emissive layer / layer for simultaneous electron transport and electron injection / cathode

[0274] (7) Anode / Hole transport layer / Electron blocking layer / Emitting layer / Electron transport layer / Cathode

[0275] (8) Anode / Hole transport layer / Electron blocking layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode

[0276] (9) Anode / hole injection layer / hole transport layer / electron blocking layer / emissive layer / electron transport layer / cathode

[0277] (10) Anode / hole injection layer / hole transport layer / electron blocking layer / emissive layer / electron transport layer / electron injection layer / cathode

[0278] (11) Anode / hole transport layer / emissive layer / hole blocking layer / electron transport layer / cathode

[0279] (12) Anode / hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0280] (13) Anode / hole injection layer / hole transport layer / emissive layer / hole blocking layer / electron transport layer / cathode

[0281] (14) Anode / hole injection layer / hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0282] (15) Anode / hole injection layer / hole transport layer / emissive layer / hole blocking layer / layer that performs electron transport and electron injection simultaneously / cathode

[0283] (16) Anode / hole injection layer / hole transport layer / electron blocking layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0284] The structure of the organic light-emitting device of the present specification may have a structure such as that shown in FIGS. 1 to 3, but is not limited thereto.

[0285] In FIG. 1, an anode (2), a light-emitting layer (3), and a cathode (4) are sequentially stacked on a substrate (1).

[0286] The structure of an organic light-emitting device is exemplified. In such a structure, the compound may be included in the light-emitting layer (3).

[0287] FIG. 2 illustrates 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), a layer (8) that simultaneously transports and injects electrons, and a cathode (4) are sequentially stacked on a substrate (1). In such a structure, the compound may be included in the layer (8) that simultaneously transports and injects electrons or the light-emitting layer (7).

[0288] FIG. 3 illustrates 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), a hole blocking layer (9), a layer (8) that simultaneously transports and injects electrons, and a cathode (4) are sequentially stacked on a substrate (1). In such a structure, the compound may be included in the hole blocking layer (9), the layer (8) that simultaneously transports and injects electrons, or the light-emitting layer (7).

[0289] For example, an organic light-emitting device according to the present invention can be manufactured by using a physical vapor deposition (PVD) method, such as sputtering or electron beam evaporation, to deposit a metal or a conductive metal oxide or an alloy thereof onto a substrate to form an anode, and then forming an organic layer thereon comprising a hole injection layer, a hole transport layer, an emitting layer, an electron blocking layer, a hole suppression layer, and a layer that simultaneously performs electron transport and electron injection, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto a substrate.

[0290] 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 performs electron transport and electron injection, an electron blocking layer, an emitting layer and an electron transport layer, an electron injection layer, a layer that simultaneously performs hole injection and hole transport, etc., but is not limited thereto and may be a single layer structure. In addition, the above organic layer may be manufactured with a smaller number of layers by using various polymer materials and a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0291] The above-mentioned anode is an electrode that injects holes, and as the anode material, it is generally preferable to use an organic layer with a high work function to facilitate hole injection. Specific examples of anode materials that can be used in the present invention 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; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0292] The above-mentioned cathode is an electrode for injecting electrons, and as the cathode material, it is preferable to have a material with a low work function to facilitate electron injection, typically an organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0293] The hole injection layer described above is a layer that facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material capable of receiving holes well from the anode at low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers of polyaniline and polythiophene series, but are not limited to these.

[0294] The hole transport layer described above can facilitate the transport of holes. Suitable hole transport materials are those capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer, provided they possess high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0295] An electron blocking layer may be provided between the hole transport layer and the light-emitting layer. The electron blocking layer is a layer capable of improving the lifespan and efficiency of the device by preventing holes injected from the hole injection layer from passing through the light-emitting layer and entering the electron injection layer, and the aforementioned compound or a material known in the art may be used.

[0296] The above-mentioned light-emitting layer may emit red, green, or blue light and may be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. If the above-mentioned organic light-emitting device includes an additional light-emitting layer in addition to the light-emitting layer containing the compound represented by Chemical Formula 1 described above, the additional light-emitting layer may emit red, green, or blue light and may be composed of a phosphorescent material or a fluorescent material. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole, and benzimidazole series; poly(p-phenylenevinylene) (PPV) series polymers; and spiro compounds. Examples include polyfluorene and rubrene, but are not limited to these.

[0297] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0298] When the emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the light-emitting layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distrylarylene (DSA), PFO-based polymers, and PPV-based polymers may be used as light-emitting dopants, but are not limited to these.

[0299] A hole suppression layer may be provided between the electron transport layer and the light-emitting layer, and the 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, hole suppression materials include triazine derivatives, phenanthroline derivatives, BCP, etc., but are not limited thereto, and materials known in the art may be used.

[0300] The electron transport layer described above can facilitate the transport of electrons. As an electron transport material, a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility, is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes, but are not limited to these. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from degrading, and if it is 50 nm or less, there is an advantage in preventing the driving voltage from rising to improve electron transport due to the electron transport layer being too thick.

[0301] The electron injection layer described above can facilitate the injection of electrons. As an electron injection material, a compound is preferred that has the ability to transport electrons, has an excellent electron injection effect from the cathode, an excellent electron injection effect on the emissive layer or emissive material, prevents the movement of excitons generated in the emissive layer to the hole injection layer, and also has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0302] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, Examples include bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited thereto.

[0303] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0304] Hereinafter, experimental examples will be described in detail to specifically explain the present specification. However, the embodiments according to the present specification may be modified in various different forms, and the scope of the present application is not to be interpreted as being limited to the embodiments described below. The embodiments of the present application are provided to more completely explain the present specification to those with average knowledge in the art.

[0305] Preparation Example 1-1 <Preparation of Compound C1>

[0306]

[0307] Compound P1-A (50.39 g, 131.49 mmol) and Compound B (40.1 g, 157.8 mmol) were added to 600 ml of dioxane under a nitrogen atmosphere and stirred. Then, potassium acetate (38.7 g, 394.47 mmol) was added, the temperature was gradually increased and refluxed, and 100 ml of dioxane was distilled under reduced pressure. Afterward, [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride (Pd(dppf)Cl2, 1.92 g, 2.63 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and acetonitrile and water were added to precipitate a solid. The resulting solid was filtered, dissolved in 10 times the amount of chloroform at room temperature, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate and acidic clay were added to the separated organic layer and stirred, then filtered, and the filtrate was subjected to vacuum distillation. The solid produced during concentration was filtered to prepare a pale ivory solid compound P1 (36.2 g, yield 64%, MS: [M+H]+=431).

[0308]

[0309] Under a nitrogen atmosphere, compound P1 (18.1 g, 42.1 mmol) and compound A1 (14.5 g, 42.1 mmol) were added to 200 ml of tetrahydrofuran and stirred. Then, potassium carbonate (17.4 g, 126.24 mmol) dissolved in 70 ml of water was added and stirred thoroughly, after which the temperature was gradually increased and refluxed. Subsequently, tetrakis(triphenylphosphine) palladium (1.46 g, 1.26 mmol) was added. After a reaction of 12 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The filtered solid was dissolved in N-methyl-2-pyrrolidone at 60 times the volume of 130°C, and 4 ml of diethylenetriamine was added and stirred. The mixture was cooled to room temperature, the resulting solid was filtered, and the process was repeated one more time. Subsequently, slurry purification was performed on toluene and tetrahydrofuran, respectively, to produce a white solid compound C1 (11.3g, yield 44%, MS: [M+H]+=612).

[0310] Preparation Example 1-2 <Preparation of Compound C2>

[0311]

[0312] Compound C2 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0313] (16.5g, Yield 41%, MS: [M+H] + = 457)

[0314] Preparation Example 1-3 <Preparation of Compound C3>

[0315]

[0316] Compound C3 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0317] (22.1g, Yield 55%, MS: [M+H] + = 507)

[0318] Preparation Example 1-4 <Preparation of Compound C4>

[0319]

[0320] Compound C4 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0321] (17.4g, Yield 44%, MS: [M+H] + = 684)

[0322] Preparation Examples 1-5 <Preparation of Compound C5>

[0323]

[0324] Compound C5 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0325] (25.2g, Yield 63%, MS: [M+H] + = 546)

[0326] Preparation Example 1-6 <Preparation of Compound C6>

[0327]

[0328] Compound C6 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0329] (27.0g, Yield 68%, MS: [M+H] + = 649)

[0330] Preparation Example 1-7 <Preparation of Compound C7>

[0331]

[0332] Compound C7 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0333] (12.9g, Yield 32%, MS: [M+H] + = 702)

[0334] Preparation Example 1-8 <Preparation of Compound C8>

[0335]

[0336] Compound C8 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0337] (14.6g, Yield 37%, MS: [M+H] + = 688)

[0338] Preparation Example 1-9 <Preparation of Compound C9>

[0339]

[0340] Compound C9 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0341] (18.1g, Yield 45%, MS: [M+H] + = 612)

[0342] Preparation Example 1-10 <Preparation of Compound C10>

[0343]

[0344] Compound C10 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0345] (8.9g, Yield 22%, MS: [M+H] + = 778)

[0346] Preparation Example 1-11 <Preparation of Compound C11>

[0347]

[0348] Compound C11 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0349] (12.2g, Yield 31%, MS: [M+H] + = 713)

[0350] Preparation Example 1-12 <Preparation of Compound C12>

[0351]

[0352] Compound C12 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0353] (15.3g, Yield 38%, MS: [M+H] + = 612)

[0354] Preparation Example 1-13 <Preparation of Compound C13>

[0355]

[0356] Compound C13 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0357] (11.1g, Yield 28%, MS: [M+H] + = 688)

[0358] Preparation Example 1-14 <Preparation of Compound C14>

[0359]

[0360] Compound C14 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0361] (26.5g, Yield 66%, MS: [M+H] + = 582)

[0362] Preparation Example 1-15 <Preparation of Compound C15>

[0363]

[0364] Compound C15 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0365] (9.8g, Yield 25%, MS: [M+H] + = 637)

[0366] Preparation Example 1-16 <Preparation of Compound C16>

[0367]

[0368] Compound C16 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0369] (12.0g, Yield 30%, MS: [M+H] + = 713)

[0370] Preparation Example 1-17 <Preparation of Compound C17>

[0371]

[0372] Compound C17 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0373] (20.7g, Yield 52%, MS: [M+H] + = 737)

[0374] Preparation Example 1-18 <Preparation of Compound C18>

[0375]

[0376] Compound C18 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0377] (26.9g, Yield 67%, MS: [M+H] + = 622)

[0378] Preparation Example 1-19 <Preparation of Compound C19>

[0379]

[0380] Compound C19 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0381] (34.2g, Yield 85%, MS: [M+H] + = 562)

[0382] Preparation Example 1-20 <Preparation of Compound C2O>

[0383]

[0384] Compound C20 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0385] (30.1g, Yield 75%, MS: [M+H] + = 638)

[0386] Preparation Example 1-21 <Preparation of Compound C21>

[0387]

[0388] Compound C21 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0389] (25.4g, Yield 63%, MS: [M+H] + = 663)

[0390] Preparation Example 1-22 <Preparation of Compound C22>

[0391]

[0392] Compound C22 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0393] (33.7g, Yield 84%, MS: [M+H] + = 638)

[0394] Preparation Example 1-23 <Preparation of Compound C23>

[0395]

[0396] Compound C23 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0397] (25.5g, Yield 63%, MS: [M+H] + = 714)

[0398] Preparation Example 1-24 <Preparation of Compound C24>

[0399]

[0400] Compound C24 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0401] (18.5g, Yield 46%, MS: [M+H] + = 710)

[0402] Preparation Example 1-25 <Preparation of Compound C25>

[0403]

[0404] Compound C25 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0405] (34.3g, Yield 68%, MS: [M+H] + = 562)

[0406] Preparation Example 1-26 <Preparation of Compound C26>

[0407]

[0408] Compound C26 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0409] (36.4g, Yield 72%, MS: [M+H] + = 638)

[0410] Preparation Example 1-27 <Preparation of Compound C27>

[0411]

[0412] Compound C27 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0413] (24.0g, Yield 60%, MS: [M+H] + = 728)

[0414] Preparation Example 1-28 <Preparation of Compound C28>

[0415]

[0416] Compound C28 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0417] (23.6g, Yield 59%, MS: [M+H] + = 663)

[0418] Preparation Example 1-29 <Preparation of Compound C29>

[0419]

[0420] Compound C29 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0421] (17.5g, Yield 58%, MS: [M+H] + = 790)

[0422] Preparation Example 1-30 <Preparation of Compound C30>

[0423]

[0424] Compound C30 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0425] (29.1g, Yield 72%, MS: [M+H] + = 638)

[0426] Preparation Example 1-31 <Preparation of Compound C31>

[0427]

[0428] Compound C31 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0429] (22.0g, Yield 55%, MS: [M+H] + = 714)

[0430] Preparation Example 1-32 <Preparation of Compound C32>

[0431]

[0432] Compound C32 was prepared using the same method as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the reaction scheme above.

[0433] (27.7g, Yield 69%, MS: [M+H] + = 714)

[0434] Preparation Example 1-33 <Preparation of Compound C33>

[0435]

[0436] Compound C33 was prepared in the same manner as the preparation method of Preparation Example 1-1, except that each starting material was prepared as per the above reaction scheme.

[0437] (20.3g, Yield 50%, MS: [M+H] + = 728)

[0438] Example 1-1

[0439] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0440] A hole injection layer was formed by thermal vacuum deposition of the following compound [HI-A] to a thickness of 600 Å on the prepared ITO transparent electrode. A hole transport layer was formed by sequentially vacuum depositing hexanitrile hexaazatriphenylene (HAT) of the following chemical formula to a thickness of 50 Å and the following compound [HT-A] (600 Å) on the hole injection layer.

[0441] Next, a light-emitting layer was formed by vacuum depositing the following compounds [BH] and [BD] in a weight ratio of 25:1 on the hole transport layer with a film thickness of 200 Å.

[0442] A layer capable of simultaneous electron transport and electron injection was formed by vacuum depositing the above compound C1 and the following compound [LiQ] (Lithium quinolate) in a 1:1 weight ratio on the above light-emitting layer to form a layer with a thickness of 350 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 1,000 Å on the layer capable of simultaneous electron transport and electron injection.

[0443] In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, while the deposition rates of lithium fluoride and aluminum for the cathode were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 1 × 10⁻⁶ -7 Up to 5 × 10 -8 An organic light-emitting diode was fabricated by maintaining torr.

[0444]

[0445] Examples 1-2 to 1-33

[0446] An organic light-emitting diode was prepared in the same manner as in Example 1-1, except that the compound of Table 1 below was used instead of compound C1 in Example 1-1.

[0447] Comparative Examples 1-1 to 1-6

[0448] An organic light-emitting diode was prepared in the same manner as in Example 1-1, except that the compound of Table 1 below was used instead of compound C1 in Example 1-1.

[0449]

[0450] Organic light-emitting diodes at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time (T) when the brightness reaches 90% of the initial brightness at the current density 90 ) was measured. The results are shown in Table 1 below.

[0451] [Table 1]

[0452]

[0453]

[0454] As described in Table 1 above, the compound represented by Formula 1 according to the present specification can be used in a layer that simultaneously performs electron transport and electron injection in an organic layer of an organic light-emitting device.

[0455] When comparing Examples 1-9 to 1-33 and Comparative Examples 1-1 to 1-2 of Table 1 above, it was confirmed that when using a compound of the combination of Formula 1 and Formula 3 according to the present specification, due to the difference in the bonding positions of the substituents, it exhibited significantly superior characteristics in terms of efficiency and lifespan compared to Comparative Example 1-1, in which an aryl group was bonded to both the R14 and R19 positions of the present invention, and Comparative Example 1-2, in which a substituent was bonded only to the R3 position of the present invention.

[0456] When comparing Examples 1-1 to 1-33 and Comparative Examples 1-3 to 1-6 of Table 1 above, it was confirmed that they exhibited significantly superior characteristics in terms of efficiency and lifespan compared to organic light-emitting diodes containing compounds in which X is a diazo group, nitro group, or amino group when R1 to R20 are all hydrogen or L is a direct bond. Explanation of the symbols

[0457] 1: Substrate 2: Anode 3: Emitting layer 4: Cathode 5: Hole injection layer 6: Precision Transport Layer 7: Emissive layer 8: Layer performing simultaneous electron transport and electron injection 9: Poison blockade layer

Claims

Claim 1 Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, A is represented by the following Chemical Formula 2 or 3, [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 1 to 3, R1 to R20 are the same or different from each other and are each independently represented by hydrogen; deuterium; or the following chemical formula 4; where A is represented by chemical formula 2, at least one of R9 and R10 is represented by the following chemical formula 4; where A is represented by chemical formula 3, at least one of R15 to R18 is represented by the following chemical formula 4, [Chemical Formula 4] In the above Chemical Formula 4, L is a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkenylene group; or a substituted or unsubstituted heteroarylene group comprising one or more atoms of O, N, S, and P as heteroelements; X is deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group comprising one or more atoms of N, O, S, and P as heteroelements; m is an integer from 0 to 4; the dotted line portions of the above Chemical Formulas 2 and 3 represent the sites bonded to Chemical Formula 1; and when L is a direct bond, X is deuterium; a halogen group; a nitrile group; A substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group comprising one or more atoms of N, O, S and P as heteroatoms, wherein any one of R14 and R19 is represented by the chemical formula 4, the remainder of R14 and R19 is hydrogen, and "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; alkyl group; alkenyl group; cycloalkyl group; alkoxy group; amine group; silyl group; aryl group; and heteroaryl group, being substituted with a substituent in which two or more of the exemplified substituents are connected, or having no substituents. Claim 2 In claim 1, the chemical formula 1 is a compound that is any one of the following chemical formulas 5 and 6: [Chemical Formula 5] [Chemical Formula 6] In the above chemical formulas 5 and 6, R1 to R20 are as defined in claim 1. Claim 3 In claim 1, L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a fluorenylene group substituted or unsubstituted with an alkyl group; a substituted or unsubstituted pyridinylene group; a substituted or unsubstituted triazinylene group; a substituted or unsubstituted thiophenylene group; a substituted or unsubstituted furanilene group; a substituted or unsubstituted dibenzothiophenylene group; a substituted or unsubstituted dibenzofuranilene group; a substituted or unsubstituted pyrimidinylene group; or a substituted or unsubstituted carbazolilene group, and "substituted or unsubstituted" is a deuterium; a halogen group; a nitrile group; a nitro group; an alkyl group; an alkenyl group; a cycloalkyl group; an alkoxy group; an amine group; a silyl group; an aryl group; A compound that means being substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl groups, being substituted with a substituent in which two or more of the exemplified substituents are connected, or having no substituents. Claim 4 A compound according to claim 1, wherein X is deuterium; a nitrile group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; a substituted or unsubstituted amine 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 comprising one or more atoms of N, O, S and P as heteroelements, and "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; an alkyl group; an alkenyl group; acycloalkyl group; an alkoxy group; an amine group; a silyl group; an aryl group; and a heteroaryl group, being substituted with a substituent in which two or more of the exemplified substituents are connected, or having no substituents. Claim 5 A compound according to claim 1, wherein where L is a direct bond, X is deuterium; a nitrile 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 fluorenyl group; a substituted or unsubstituted triazine group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group, wherein "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; an alkyl group; an alkenyl group; a cycloalkyl group; an alkoxy group; an amine group; a silyl group; an aryl group; and a heteroaryl group, being substituted with a substituent in which two or more of the exemplified substituents are connected, or having no substituents. Claim 6 delete Claim 7 delete Claim 8 In claim 1, the compound of formula 1 is a compound that is any one of the following compounds: . Claim 9 An organic electronic device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound according to any one of claims 1 to 5 and 8. Claim 10 The organic electronic device according to claim 9, wherein the organic layer comprises a layer that simultaneously performs electron transport and electron injection, and the layer that simultaneously performs electron transport and electron injection comprises the compound. Claim 11 An organic electronic device according to claim 9, wherein the organic layer comprises a hole blocking layer, and the hole blocking layer comprises the compound. Claim 12 An organic electronic device according to claim 9, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound. Claim 13 An organic electronic device according to claim 9, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as a host of the light-emitting layer. Claim 14 In claim 9, the organic electronic device is an organic electronic device selected from the group consisting of an organic light-emitting device, an organic phosphorescent device, an organic solar cell, an organic photosensitive material (OPC), and a glass transistor.

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