Organic compound and organic light-emitting device comprising same

Abstract

The organic compound represented by Chemical Formula 1 of the present invention can achieve excellent hole transport characteristics. In addition, a hole transport layer or a hole transport auxiliary layer of the organic light-emitting device of the present invention comprises the organic compound represented by Chemical Formula 1 of the present invention, thereby improving driving voltage, efficiency, and lifespan characteristics of the organic light-emitting device.

Description

Technical Field

[0001] The present invention relates to an organic compound and an organic light-emitting device comprising the organic compound. Background Art

[0002] Compared with other flat panel display devices such as existing liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), organic light-emitting devices (OLEDs) have a simpler structure and various advantages in manufacturing processes. They have excellent high brightness and viewing angle characteristics, fast response speed, and low driving voltage. Therefore, they are being actively developed and commercialized in order to be used in flat panel displays such as wall-mounted TVs or as backlights, lighting, advertising boards, and other light sources for displays.

[0003] Organic light-emitting devices (OLEDs) consist of an organic layer between two electrodes. They operate on the principle that electrons and holes are injected into the light-emitting layer from the two electrodes. The electrons and holes combine to form excitons, which then drop from an excited state to a ground state, generating light.

[0004] An organic light-emitting device may include at least one light-emitting layer. Typically, an organic light-emitting device having multiple light-emitting layers includes light-emitting layers that emit light with different peak wavelengths, and a specific color can be achieved by combining light with different peak wavelengths.

[0005] These organic light-emitting devices can be categorized as either front-emitting or back-emitting devices. Front-emitting devices utilize a reflective second electrode (cathode) to transmit light generated in the light-emitting layer toward a semi-transparent first electrode (anode). Conversely, back-emitting devices utilize a reflective first electrode to transmit light generated in the light-emitting layer and reflected by the first electrode toward a transparent second electrode, which drives the thin-film transistor.

[0006] Prior art literature

[0007] Patent Literature

[0008] Existing Patent Document 1: KR10-2523173B1

[0009] Existing Patent Document 2: WO2020-111253A1

[0010] Existing Patent Document 3: WO2017-099471A1 Summary of the Invention

[0011] Problems to be solved by the invention

[0012] The object of the present invention is to provide a novel organic compound and an organic light-emitting device comprising the organic compound.

[0013] In addition to the above technical problems, the embodiments according to the present invention can also be used to solve other technical problems not specifically mentioned.

[0014] The present invention is not limited to the above-mentioned purpose, and other purposes and advantages of the present invention not set forth can be understood by the following description and will be more clearly understood by the embodiments of the present invention. In addition, it is easy to understand that the purposes and advantages of the present invention can be achieved by the means and combinations thereof shown within the scope of the claims.

[0015] Means used to solve problems

[0016] In order to solve the technical problem, according to one embodiment of the present invention, an organic compound having a novel structure represented by the following Chemical Formula 1 may be provided. The definition of the following Chemical Formula 1 is the same as that described in the present specification and claims.

[0017] [Chemical Formula 1]

[0018]

[0019] According to another embodiment of the present invention, an organic light-emitting device may be provided, comprising: a first electrode; a second electrode opposite to the first electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein at least one of the one or more organic layers is an organic layer comprising a compound represented by Chemical Formula 1.

[0020] Effects of the Invention

[0021] The organic compound represented by Chemical Formula 1 of the present invention may achieve excellent hole transport properties.

[0022] In addition, the organic light-emitting device of the present invention includes a hole transport layer and / or a hole transport auxiliary layer comprising the organic compound represented by Chemical Formula 1 of the present invention, which can improve the driving voltage, efficiency and lifespan characteristics of the organic light-emitting device.

[0023] In addition, when the organic compound represented by Chemical Formula 1 of the present invention is used as a hole transport auxiliary layer material, it can have a suitable energy level as a hole transport auxiliary layer, which has the function of transporting holes from the hole transport layer to the light-emitting layer and blocking electrons transferred from the light-emitting layer.

[0024] Furthermore, the organic light-emitting device of the present invention is a hole transport layer and / or a hole transport auxiliary layer comprising the organic compound represented by Chemical Formula 1 of the present invention, and can excellently achieve the target color coordinates of the light-emitting layer even when combined with a light-emitting layer of any color.

[0025] The effects of this specification are not limited to the effects proposed above, and those skilled in the art can clearly understand other effects not proposed from the following description. DETAILED DESCRIPTION

[0026] Hereinafter, the above-mentioned objects, features and advantages are described in detail, so that those skilled in the art can easily implement the technical concept of the present invention.

[0027] When describing this specification, when it is judged that the detailed description of the related known technology may unnecessarily obscure the gist of this specification, its detailed description is omitted.

[0028] When using the terms "including," "having," "forming," "arranged," or "equipped" in this specification, other parts may be added unless "to only" is used. Unless otherwise specified, when a component is expressed in the singular, the plural number is also included.

[0029] In this specification, when explaining constituent elements, even if there is no additional clear description, it is to be construed that the error range is included.

[0030] In this specification, setting an arbitrary structure on the "upper part (or lower part)" of a constituent element or "above (or below)" of a constituent element may not only refer to a situation in which the arbitrary structure is set in contact with the upper surface (or lower surface) of the constituent element, but may also refer to a situation in which other structures may be interposed between the constituent element and the arbitrary structure set above (or below) the constituent element.

[0031] The term "halogen group" used in the present specification includes fluorine, chlorine, bromine and iodine.

[0032] The term "alkyl" as used herein refers to both straight-chain and branched alkyl radicals. Unless otherwise specified, an alkyl group may contain from 1 to 30 carbon atoms and may include, but is not limited to, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, and hexyl. Furthermore, the alkyl group may be arbitrarily substituted.

[0033] The term "cycloalkyl" as used herein refers to a cyclic alkyl radical. Unless otherwise specified, the cycloalkyl group contains 3 to 20 carbon atoms and may include, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, and the like. In addition, the cycloalkyl group may be arbitrarily substituted.

[0034] The term "alkenyl" as used herein refers to straight-chain and branched alkenyl radicals having at least one carbon-carbon double bond. Unless otherwise specified, alkenyl groups contain 2 to 30 carbon atoms and include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl. Alkenyl groups may be arbitrarily substituted.

[0035] The term "cycloalkenyl" as used herein refers to a cyclic alkenyl radical. Unless otherwise specified, a cycloalkenyl radical contains 3 to 20 carbon atoms and may be optionally substituted.

[0036] The term "alkynyl" as used herein refers to straight-chain and branched alkyne radicals having at least one carbon-carbon triple bond. Unless otherwise specified, an alkynyl group contains 2 to 30 carbon atoms and may include, but is not limited to, ethynyl, 2-propynyl, and the like. In addition, an alkynyl group may be arbitrarily substituted.

[0037] The term "cycloalkynyl" as used herein refers to a cyclic alkynyl radical. Unless otherwise specified, a cycloalkynyl radical contains 3 to 20 carbon atoms and may be optionally substituted.

[0038] As used herein, the terms "arylalkyl" or "aralkyl" are used interchangeably and refer to an alkyl group having an aromatic group as a substituent. In addition, the arylalkyl group (aralkyl group) may be optionally substituted.

[0039] The terms "aryl" or "aromatic group" used in this specification are used as the same meaning, and aryl includes monocyclic groups and polycyclic groups. Polycyclic can include "condensed rings" as two or more rings (two adjacent rings share two carbons). In addition, it can also include a form in which more than two rings are simply attached or condensed to each other. If not particularly limited, the aryl group contains 6 to 30 carbon atoms and can include but is not limited to phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl (spirofluorenyl) etc. In addition, the aryl group can be substituted arbitrarily.

[0040] The terms "heteroaryl" or "heteroaromatic group" used in this specification are used as the same meaning, and heteroaryl includes monocyclic groups and polycyclic groups. Polycyclic rings may include "fused rings", which are two or more rings in which two adjacent rings share two carbon or heteroatoms. In addition, it may also include a form in which two or more rings are simply attached or condensed to each other. If not particularly limited, the heteroaryl group contains 5 to 60 carbon atoms. When the carbon atom is 1 or 2, the ring may be formed by containing additional heteroatoms. In addition, the heteroaryl group may contain 5 to 60 carbon atoms, in which case at least one carbon in the ring is substituted by a heteroatom such as oxygen (O), nitrogen (N), sulfur (S) or selenium (Se), and may include, but is not limited to, six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathiyl, indolizinyl, indolyl, purinyl, quinolyl, isoquinolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, phenylcarbazole, 9-phenylcarbazole, and carbazole; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, and 2-pyrimidinyl. In addition, the heteroaryl group may be arbitrarily substituted.

[0041] The term "heterocyclic group" as used herein refers to a group in which at least one of the carbon atoms constituting an aryl group, cycloalkyl group, cycloalkenyl group, cycloalkynyl group, aralkyl group, arylamino group, etc. is substituted with a heteroatom such as oxygen (O), nitrogen (N), sulfur (S), or selenium (Se). With reference to the above definition, the group may include, but is not limited to, heteroaryl groups, heterocycloalkyl groups, heterocycloalkenyl groups, heterocycloalkynyl groups, heteroaralkyl groups, and heteroarylamino groups. Furthermore, the heterocyclic group may be arbitrarily substituted.

[0042] The term "carbon ring" used in the present specification may be used as a term including "cycloalkyl" as an alicyclic group and "aryl (aromatic group)" as an aromatic ring group, unless otherwise limited.

[0043] The terms "heteroalkyl" and "heteroaralkyl" as used in this specification refer to groups in which at least one of the carbon atoms constituting the alkyl and aralkyl groups is substituted with a heteroatom such as oxygen (O), nitrogen (N), sulfur (S) or selenium (Se). In addition, the heteroalkyl and heteroaralkyl groups may be arbitrarily substituted.

[0044] The terms "alkylamino", "aralkylamino", "arylamino" and "heteroarylamino" used in this specification refer to amino groups (or amine groups) substituted with the alkyl, aralkyl, aryl and heteroaryl groups, and include primary, secondary and tertiary amino groups (or amine groups). In addition, alkylamino groups, arylalkylamino groups, arylamino groups and heteroarylamino groups may be arbitrarily substituted.

[0045] The terms "alkylsilyl", "arylsilyl", "alkoxy", "aryloxy", "alkylthio" and "arylthio" used in this specification refer to silyl, oxy and thio groups substituted with the alkyl and aryl groups respectively. In addition, the alkylsilyl, arylsilyl, alkoxy, aryloxy, alkylthio and arylthio groups may be arbitrarily substituted.

[0046] The terms "arylene," "arylalkylene," "heteroarylene," and "heteroarylalkylene" as used herein refer to divalent substituents of the aforementioned aryl, arylalkyl, heteroaryl, and heteroarylalkyl groups, each of which further includes one substitution. Furthermore, the arylene, arylalkylene, heteroarylene, and heteroarylalkylene groups may be arbitrarily substituted.

[0047] The term "substituted" as used in this specification means that a hydrogen (H) atom bonded to a carbon or nitrogen atom of the compound of the present invention is replaced by a substituent other than hydrogen. When multiple substituents are present, each substituent may be the same or different.

[0048] The substituents defined in the present specification may be selected from deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilyl (TMS), alkyl groups having 1 to 30 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, alkenyl groups having 2 to 30 carbon atoms, cycloalkenyl groups having 3 to 20 carbon atoms, alkynyl groups having 2 to 30 carbon atoms, cycloalkynyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, aralkyl groups having 7 to 30 carbon atoms, heteroaryl groups having 5 to 60 carbon atoms, and heteroaryl groups having 6 to 60 carbon atoms. The present invention further comprises at least one selected from the group consisting of a heteroarylalkyl group having 1 to 0 carbon atoms, an amino group, an alkylamino group having 1 to 30 carbon atoms, an arylalkylamino group having 7 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 5 to 60 carbon atoms, a silyl group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, and an arylthio group having 6 to 30 carbon atoms.

[0049] Each object and substituent defined in this specification may be the same or different, unless otherwise specified.

[0050] The units used in this specification are based on weight (wt) unless otherwise specified. For example, when "%" is described, it is interpreted as weight % (wt%).

[0051] Hereinafter, an organic compound according to the present invention and an organic light-emitting device including the same are described in detail.

[0052] The organic compound according to one embodiment of the present invention may be represented by the following Chemical Formula 1.

[0053] [Chemical Formula 1]

[0054]

[0055] in,

[0056] X1 can be oxygen (O) or sulfur (S),

[0057] m can be an integer from 0 to 9,

[0058] n can be an integer from 0 to 6,

[0059] L1 and L2 may be the same as or different from each other, and are each independently selected from the group consisting of a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylene group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms, and a substituted or unsubstituted heteroarylalkylene group having 6 to 60 carbon atoms.

[0060] Ar1 may be selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms.

[0061] Ar2 may be an oxygen-containing or sulfur-containing substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms,

[0062] R1 and R2 may be the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms.

[0063] The substituents of L1, L2, Ar1, Ar2, R1 and R2 may be independently selected from deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilyl (TMS), alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, alkenyl having 2 to 30 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, alkynyl having 2 to 30 carbon atoms, cycloalkynyl having 3 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, heteroaryl having 5 to 60 carbon atoms, heteroaryl having 6 to 60 carbon atoms, At least one selected from the group consisting of an alkyl group, an amino group, an alkylamino group having 1 to 30 carbon atoms, an arylalkylamino group having 7 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 5 to 60 carbon atoms, a silyl group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, and an arylthio group having 6 to 30 carbon atoms; when the group has a plurality of such substituents, the substituents may be the same or different.

[0064] In Chemical Formula 1, L1 and L2 may be the same or different, and may each independently be a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms.

[0065] In Chemical Formula 1, L1 and L2 may be the same or different, and may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazole group.

[0066] The substituents of L1 and L2 may each independently be at least one selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, dimethylfluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazine, dibenzofuranyl, dibenzothiophenyl, carbazole, and n-phenylcarbazole (9-phenylcarbazole).

[0067] In Chemical Formula 1, Ar1 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazole group.

[0068] The substituent of Ar1 may be at least one selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, dimethylfluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazine, dibenzofuranyl, dibenzothiophenyl, carbazole, and n-phenylcarbazole (9-phenylcarbazole).

[0069] In the Chemical Formula 1, Ar2 may be a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0070] The substituent of Ar2 may be at least one selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, dimethylfluorenyl, spirofluorenyl, pyridyl, pyrimidinyl, triazine, dibenzofuranyl, dibenzothiophenyl, carbazole, and n-phenylcarbazole (9-phenylcarbazole).

[0071] According to one embodiment of the present invention, the organic compound of Chemical Formula 1 may be represented by the following Chemical Formula 2 or 3.

[0072] [Chemical Formula 2]

[0073]

[0074] [Chemical Formula 3]

[0075]

[0076] In the Chemical Formula 2 or Chemical Formula 3,

[0077] m, n and X1 are as defined in Chemical Formula 1,

[0078] L1, L2, Ar1, R1 and R2 and their substituents have the same meanings as those defined in Chemical Formula 1.

[0079] X2 can be oxygen (O) or sulfur (S),

[0080] o1 can be an integer from 0 to 7,

[0081] o2 can be an integer from 0 to 5,

[0082] R3 may be the same as or different from each other and may be each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms.

[0083] The substituents of R3 may be independently selected from deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilyl (TMS), alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, alkenyl having 2 to 30 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, alkynyl having 2 to 30 carbon atoms, cycloalkynyl having 3 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, heteroaryl having 5 to 60 carbon atoms, heteroaralkyl having 6 to 60 carbon atoms, amino, carbonyl, The substituents may be at least one selected from the group consisting of an alkylamino group having 1 to 30 carbon atoms, an arylalkylamino group having 7 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 5 to 60 carbon atoms, a silyl group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms and an arylthio group having 6 to 30 carbon atoms. When a plurality of substituents are present, the substituents may be the same or different.

[0084] In Chemical Formulas 1, 2, and 3, the phenanthrene group and the nitrogen atom (N) may be located at the meta position or the para position relative to the ring containing X1. Such a positional relationship can provide excellent hole transport properties for the organic compound and improve the driving voltage, efficiency, and lifespan of the organic light-emitting device.

[0085] According to one embodiment of the present invention, the organic compound of Chemical Formula 1 may be represented by the following Chemical Formulas 4 to 63.

[0086] In the following Chemical Formulas 4 to 63,

[0087] m, n, o1, o2, X1 and X2 have the same meanings as those defined in Chemical Formulas 1 to 3,

[0088] L1, L2, Ar1, R1, R2 and R3 and their substituents have the same meanings as defined in Chemical Formulas 1 to 3.

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] According to one embodiment of the present invention, Chemical Formulas 1 to 63 of the present invention may be represented by a combination of chemical formulas represented by the following Chemical Formula A, Chemical Formula B, Chemical Formula C, Chemical Formula D, or Chemical Formula E.

[0095] In the following Chemical Formulas A to E, X1 and X2 are as defined in Chemical Formulas 1 to 3, and L1, L2, Ar1 and Ar2 and their substituents are as defined in Chemical Formulas 1 to 3.

[0096] The “*” in the following chemical formula C indicates that the nitrogen atom is bonded to another chemical formula.

[0097]

[0098] For example, in the compound according to one embodiment of the present invention, position 9 of Chemical Formula A is bound to position 4 of Chemical Formula B, position 1 of Chemical Formula B is bound to the nitrogen atom of Chemical Formula C, and any one of positions 1 to 4 and positions 6 to 9 of Chemical Formula D is bound to L2. The compound can be represented by Chemical Formula 4.

[0099] For example, a compound in which position 9 of Chemical Formula A is bound to position 4 of Chemical Formula B, position 1 of Chemical Formula B is bound to the nitrogen atom of Chemical Formula C, and any position from positions 2 to 7 of Chemical Formula E is bound to L2 can be represented by Chemical Formula 10.

[0100] In the compound according to one embodiment of the present invention, when referring to the molecular energy level, for the phenanthrene group of Chemical Formula A and the aromatic amine group of Chemical Formula C in Chemical Formula B, in the case of a 1-4 or 4-1 combination based on the para position of Chemical Formula B, it can be suitable for a blue device, and in the case of a 1-3 or 3-1 combination based on the meta position of Chemical Formula B and a 2-4 or 4-2 combination, it can be suitable for a green device.

[0101] In the compound according to one embodiment of the present invention, Chemical Formula B includes the phenanthryl group of Chemical Formula A, so that the conjugated system or delocalized bond can be further stretched compared to a compound including a phenyl group or a naphthyl group instead of the phenanthryl group, and thus can be more stable.

[0102] According to one embodiment of the present invention, for example, the compounds of the present invention are compounds of Chemical Formulas 4 to 63 in which Chemical Formula B is bonded to the phenanthrene unit of Chemical Formula A and the aromatic amine nitrogen unit of Chemical Formula C at the para or meta position. Compared with compounds bonded at the ortho position, the steric strain is smaller and thus the compounds can be more stable.

[0103] In addition, in the compound according to one embodiment of the present invention, at least one of Ar1 or Ar2 in Chemical Formula C includes a dibenzofuranyl group or a dibenzothiophenyl group (Chemical Formula D) or a benzofuranyl group or a benzothiophenyl group (Chemical Formula E), and therefore, compared with a compound not including these, it can have excellent thermal stability and has a higher hole transport ability, and therefore the efficiency as a hole transport material may be higher.

[0104] According to one embodiment of the present invention, the organic compound represented by Chemical Formula 1 may be selected from the group consisting of the following compounds.

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139] An organic light emitting device according to an embodiment of the present invention includes a first electrode (anode) and a second electrode (cathode) opposite to the first electrode, and may include one or more organic layers between the first electrode and the second electrode.

[0140] At least one of the one or more organic layers may include the organic compound represented by Chemical Formula 1.

[0141] The organic layer may include at least one layer selected from the group consisting of a hole injection layer (HIL), a hole transport layer (HTL), a hole transport auxiliary layer (HTL), an emitting layer (EML), an electron transport auxiliary layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL).

[0142] For example, an organic light-emitting device may have a structure in which a first electrode, a hole injection layer (HIL), a hole transport layer (HTL), a hole transport auxiliary layer (HTL), an emission layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), and a second electrode are stacked in sequence.

[0143] In addition, the organic light emitting device may have a first electrode, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an emission layer (EML), an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a second electrode stacked in sequence.

[0144] The organic layer including the compound represented by Chemical Formula 1 according to one embodiment of the present invention may be a hole transport layer (HTL) or a hole transport auxiliary layer (HTL).

[0145] The one or more organic layers may further include at least one selected from the group consisting of a hole injection layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

[0146] For example, when the organic compound represented by Chemical Formula 1 is used as a hole transport auxiliary layer material, it may have a suitable energy level as a hole transport auxiliary layer, which plays the role of transporting holes from the hole transport layer to the light emitting layer and blocking electrons transferred from the light emitting layer.

[0147] In the organic light-emitting device according to one embodiment of the present invention, the hole transport layer and / or the hole transport auxiliary layer including the organic compound represented by Chemical Formula 1 can excellently achieve target color coordinates even when combined with a light-emitting layer of any color.

[0148] The first electrode may be an anode, and the first electrode may include transparent and highly conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), and zinc oxide (ZnO).

[0149] The second electrode may be a cathode, and the second electrode may include materials such as lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). In addition, in the case of a front-emitting organic light-emitting device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent second electrode capable of transmitting light.

[0150] A capping layer (CPL) may be formed on the surface of the second electrode using a composition for forming a capping layer.

[0151] Furthermore, a protective film (encapsulation layer or protective layer) may be provided on the cover layer to protect the organic light-emitting device from moisture and oxygen. These protective films may be formed from a curable adhesive composition containing an inorganic moisture absorbent.

[0152] The hole injection layer or hole transport layer compound is not particularly limited, and any compound can be used as long as it is generally used as a hole injection layer or hole transport layer compound. Non-limiting examples of hole injection layer or hole transport layer compounds include phthalocyanine derivatives, porphyrin derivatives, triarylamine derivatives, indole and carbazole derivatives, etc. For example, 1,4,5,8,9,11-hexaazatriphenylhexanitrile (HAT-CN), copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA), N4,N4,N4',N4'-tetrakis([1,1'-biphenyl]-1,1'-diphenylamine ... N,N'-di(naphthyl-1-yl)-N,N'-biphenyl-benzidine (NPB), N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), etc.

[0153] The compound contained in the light-emitting layer is not particularly limited, and any compound can be used as long as it is generally used as a light-emitting layer compound. A single light-emitting compound or a light-emitting host compound can be used.

[0154] As the luminescent compound of the luminescent layer, a compound that causes luminescence by phosphorescence, fluorescence, thermally activated delayed fluorescence (TADF, also known as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes may be included, but is not limited thereto. The luminescent compound may be selected from a variety of materials according to the desired luminescent color. As non-limiting examples of the luminescent compound, phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and fused ring derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, diazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyryl derivatives, bisstyrylarylene derivatives, diazaindacenyl derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives, dibenzofuran derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, anthocyanine derivatives, oxybenzanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, quinolone derivatives, acridine derivatives, oxazine derivatives, phenylene ether derivatives oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, pyrene derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, benzofluorene derivatives, aromatic boron derivatives, aromatic nitrogen boron derivatives and metal complexes (complexes in which metals such as Ir, Pt, Au, Eu, Ru, Re, Ag and Cu are bound to heteroaromatic ring ligands, etc.), etc.For example, N1,N1,N6,N6-tetrakis(4-(1-silyl)phenyl)pyrene-1,6-diamine, 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-boronaphtho[3,2,1-de]anthracene (t-DABNA-dtB), platinum octaethylporphyrin (Pt OEP), Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(a cac)、Ir(btp)2(acac)、Ir(2-phq)3、Hex-Ir(phq)3、Ir(fbi)2(acac)、fac-Tris(2-(3-p-xylyl)phenyl)pyridine iridium(III))、Eu(dbm)3(Phen)、Ir(piq)3、Ir(piq2(acac) c), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(BT)2(acac), Ir(DMP)3, Ir(Mphq)3IR(phq)2tpy, fac-Ir(p py)2Pc, Ir(dp)PQ2, Ir(Dpm)(Piq)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, FIrpic, etc.

[0155] As the host compound of the light-emitting layer, a light-emitting host, a hole transport host, and an electron transport host or a combination thereof can be used. As non-limiting examples of the light-emitting host compound, condensed ring derivatives such as anthracene or pyrene, bisstyryl anthracene derivatives or distyryl benzene derivatives such as bisstyryl derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, n-phenylcarbazole (9-phenylcarbazole) derivatives, carbazole nitrile derivatives, etc. can be cited. As non-limiting examples of hole transport host substances, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, triarylamine derivatives, indolecarbazole derivatives, and benzoxazine and phenoxazine derivatives can be cited. As non-limiting examples of electron transport host substances, pyridine derivatives, triazine derivatives, phosphine oxide derivatives, benzofuran pyridine derivatives, and dibenzoxacillin derivatives can be cited. For example, including 9,10-bis(2-naphthyl)anthracene (AND), tris(8-hydroxyquinoline)aluminum (Alq3), BAlq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis(2,2-distyryl)-1,1'-biphenyl) series, spiro-DPVBi (spiro-4,4'-bis(2,2-distyryl)-1,1'-biphenyl), LiPBO (2-(2-benzoxazolyl)-phenol lithium salt), bis(distyryl)benzene, aluminum-quinoline metal complexes, imidazole, thiazole and oxazole metal complexes, etc.

[0156] The electron injection layer or electron transport layer compound is not particularly limited, and generally, any compound can be used as long as it is used as an electron injection layer or electron transport layer compound. Non-limiting examples of the electron injection layer or electron transport layer compound include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, pyrene derivatives, coumarin derivatives, naphthalene dicarboximide derivatives, anthraquinone derivatives, diphenoquinone derivatives, dibenzoquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, diazole derivatives, metal complexes of oxin derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzopyrrole derivatives, and the like. Examples of the present invention include pyrazole compounds, gallium complexes, pyrazole derivatives, perfluorophenylene derivatives, triazine derivatives, pyrazine derivatives, benzquinoline derivatives, imidazopyridine derivatives, borane derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives, naphthyridine derivatives, aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisphenylvinyl derivatives, quinolinol metal complexes, hydroxyazole metal complexes, azomethine metal complexes, tropolone metal complexes, flavonol metal complexes, benzquinoline metal complexes, and metal salts. These materials may be used alone or in combination with other materials. For example, materials such as 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benz[d]imidazole, tris(8-hydroxyquinoline)aluminum (Alq3), LiF, Liq, Li2O, BaO, NaCl, and CsF may be included.

[0157] The electron transport auxiliary layer (ETA) compound between the ETL and the EL is not particularly limited, and any compound commonly used as an ETA compound may be used. For example, the ETA may include a pyrimidine derivative.

[0158] The organic light emitting device according to one embodiment of the present invention may be a front-emitting device or a back-emitting device.

[0159] The organic light emitting device according to one embodiment of the present invention may be used in a display device.

[0160] The organic light emitting device according to one embodiment of the present invention may be applied to a transparent display device, a mobile display device, a flexible display device, etc., but is not limited thereto.

[0161] Hereinafter, representative examples will be given to describe the synthesis methods of the compounds. However, the synthesis methods of the compounds of the present invention are not limited to the methods exemplified below.

[0162] X1, L1, L2, Ar1 and Ar2 described in the following Reactant 1, Reactant 2 and Product are as defined in Chemical Formula 1.

[0163] In the following reaction formulae, solvents, catalysts, etc. are representative examples, and any solvents, catalysts, etc. equivalent thereto may be used.

[0164] Synthesis example

[0165] The product of the present invention can be synthesized according to the following reaction formula 1, but is not limited thereto.

[0166] <Reaction Formula 1>

[0167]

[0168] The reaction of P1 in Table 1 can be performed as follows, but is not limited thereto.

[0169] Under nitrogen flow, reactant 1 (26.4 mmol) of P1, reactant 2 (25.1 mmol) of P1, t-BuONa (50.2 mmol), Pd2(dba)3 (0.53 mmol), Sphos (1.06 mmol) and toluene were added to a 500 mL flask and stirred at reflux. After completion of the reaction, the organic layer was extracted with toluene and water. The extracted solution was treated with MgSO4 to remove residual moisture, concentrated under reduced pressure, purified by column chromatography, and then recrystallized to obtain the product of P1. The synthesis results of the product of P1 are shown in Table 1 below.

[0170] In addition, in the product synthesis method, for reactant 1 and reactant 2 of P1, except using reactant 1 and reactant 2 of P2 to P57 in Table 1 below, the products of P2 to P57 were synthesized by the same method as above, and the synthesis results are shown in Table 1 below.

[0171] Table 1

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182] Experimental Example 1 – Determination of HOMO and LUMO

[0183] The role of the hole transport auxiliary layer is to reduce the holes accumulated at the interface of the light-emitting layer due to the HOMO energy level difference between the hole transport layer and the light-emitting layer. Therefore, it is preferred that the HOMO energy difference between the hole transport auxiliary layer and the light-emitting layer is smaller than the HOMO energy difference between the hole transport layer and the light-emitting layer.

[0184] Furthermore, in order to minimize the leakage of electrons from the light-emitting layer to the hole transport layer, the hole transport layer needs to have a LUMO level higher than that of the light-emitting layer.

[0185] To confirm whether the compound represented by Chemical Formula 1 of the present invention is suitable for use as a hole transport auxiliary layer material, the HOMO energy level (eV) and LUMO energy level (eV) were calculated using Spartan software (B3LYP DFT 6-31G* by spartan'16) and are shown in Table 2 below.

[0186] Table 2

[0187] Compound HOMO (calculation) LUMO (calculation) Compound 97 5.02 1.18 Compound 105 4.96 1.09 Compound 109 4.99 1.08 Compound 113 4.98 1.05 Compound 121 4.95 1.15 Compound 125 4.96 1.08 Compound 573 4.97 1.10 Compound 443 4.98 1.08 Compound 431 4.96 1.09 Compound 374 4.97 1.15 Compound 224 4.98 1.11 Compound 170 4.90 1.11 Compound 465 4.89 1.11 Compound 487 4.86 1.14 Compound 501 4.87 1.08 Compound 505 4.98 1.17

[0188] Example 1 - Fabrication of an organic light-emitting device (blue light-emitting layer)

[0189] Through the photo-lithography process, a substrate stacked with ITO (100nm) as the first electrode (anode) of the organic light-emitting device was divided into regions for the second electrode (cathode) and the first electrode (anode) and an insulating layer, and patterned. Then, with the purpose of increasing the work function of the first electrode (ITO) and cleaning it, UV-ozone treatment and surface treatment using O2:N2 plasma were performed.

[0190] Next, on the anode, a mixture of NDP-9 (2-(7-Dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)-malononitrile) and N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine in a ratio of 3:97 was deposited on the hole injection layer (HIL) to form a thickness of 10 nm. Next, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine was vacuum deposited on the upper portion of the hole injection layer as a hole transport layer to a thickness of 100 nm, and compound 1 was formed on the upper portion of the hole transport layer (HTL) as a hole transport auxiliary layer to a thickness of 15 nm.

[0191] On the upper portion of the hole transport auxiliary layer, 9,10-bis(2-naphthyl)anthracene (ADN) as a host and 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene as a dopant were used. A 25nm thick blue emitting layer (BLEL) was deposited using a host:dopant ratio of 97:3 by weight. A 25nm thick layer of 2-(4-(9,10-Di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (2-(4-(9,10-Di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and Liq (Liq)) was mixed in a 1:1 weight ratio as an electron transport layer (ETL). A 1nm thick electron injection layer (Liq) was deposited on top of the ETL. At the cathode, a mixture of magnesium and silver (Mg and Ag) in a 1:4 weight ratio was deposited to a thickness of 16nm. On the cathode, N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited to a thickness of 60 nm as a capping layer. A seal cap containing a moisture absorbent was attached to the capping layer using a UV-curable adhesive, and a protective film (encapsulation layer or protective layer) was formed to protect the organic light-emitting device from oxygen and moisture in the atmosphere, thereby manufacturing an organic light-emitting device.

[0192] Comparative Examples 1 to 5

[0193] Organic light-emitting devices of Comparative Examples 1 to 5 were respectively manufactured in the same manner as in Example 1, except that the material of Compound 1 used as the hole transport auxiliary layer material in Example 1 was changed to the following Compound A, Compound B, Compound C, Compound D, and Compound E. The structures of Compounds A to E used as hole transport auxiliary layer materials in Comparative Examples 1 to 5 are as follows.

[0194]

[0195] Examples 2 to 49

[0196] Organic light-emitting devices of Examples 2 to 49 were manufactured in the same manner as in Example 1, except that the material of Compound 1 used as the hole transport auxiliary layer material in Example 1 was changed to the materials listed in Table 3 below.

[0197] Experimental Example 2 - Performance Evaluation of Organic Light-Emitting Devices (Blue Devices)

[0198] For each of the organic light-emitting devices manufactured in Examples 1 to 49 and Comparative Examples 1 to 5, a 10 mA / cm 2 The driving voltage (V) and external quantum efficiency (EQE) (%) were measured by using McScience M6000 at 10 mA / cm 2 The lifespan (LT95) (hrs) was measured by driving the device at a constant current and checking the time it took for the luminance to decrease to 95% of the initial luminance. The measurement results are shown in Table 3 below.

[0199] Table 3

[0200]

[0201]

[0202] Example 50 - Fabrication of an organic light-emitting device (green light-emitting layer)

[0203] Through the photo-lithography process, a substrate layered with ITO (100nm) on which the first electrode (anode) of the seat organic light-emitting device is located is divided into regions for the second electrode (cathode) and the first electrode (anode), as well as an insulating layer, and patterned. Then, with the purpose of increasing the work function of the first electrode (ITO) and cleaning it, UV-ozone treatment and surface treatment using O2:N2 plasma were performed.

[0204] On the anode, a mixture of NDP-9 (2-(7-Dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)-malononitrile) and N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) in a ratio of 3:97 was deposited on the hole injection layer (HIL) to form a thickness of 10 nm. Next, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine was vacuum deposited on the upper portion of the hole injection layer as a hole transport layer to a thickness of 100 nm, and compound 1 was formed on the upper portion of the hole transport layer (HTL) as a hole transport auxiliary layer to a thickness of 15 nm.

[0205] On top of the hole-transport-assisting layer, a green emitting layer (EML) was deposited to a thickness of 35 nm using 4,4-N,N'-dicarbazole-biphenyl (CBP) as a host and Ir(ppy)3[tris(2-phenylpyridine)-iridium] as a dopant at a host:dopant ratio of 95:5 by weight. On top of the green emitting layer (EML), an electron transport layer (ETL) was deposited to a thickness of 25 nm using a mixture of 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and Liq at a weight ratio of 1:1. On top of the electron transport layer (ETL), Liq was deposited to a thickness of 1 nm toward the electron injection layer (EIL). Next, a mixture of magnesium and silver (Ag) at a weight ratio of 1:4 was deposited to a thickness of 16 nm as a cathode. On the cathode, N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited to a thickness of 60 nm as a capping layer. A seal cap containing a moisture absorbent was attached to the capping layer using a UV-curable adhesive, and a protective film (encapsulation layer or protective layer) was formed to protect the organic light-emitting device from oxygen and moisture in the atmosphere, thereby manufacturing the organic light-emitting device.

[0206] Comparative Examples 6 to 10

[0207] Organic light-emitting devices of Comparative Examples 6 to 10 were respectively manufactured in the same manner as in Example 50, except that the material of Compound 1 used as the hole transport auxiliary layer material in Example 50 was changed to the materials listed in Table 4 below. The structures of Compounds A to E used as hole transport auxiliary layer materials in Comparative Examples 6 to 10 were the same as those described in Comparative Examples 1 to 5.

[0208] Example 51 to Example 98

[0209] Organic light-emitting devices of Examples 51 to 98 were manufactured in the same manner as in Example 50, except that the material of Compound 1 used as the hole transport auxiliary layer material of Example 50 was changed to the materials listed in Table 4 below.

[0210] Experimental Example 3-Performance Evaluation of Organic Light-Emitting Devices (Green Devices)

[0211] For each of the organic light-emitting devices manufactured in Examples 50 to 98 and Comparative Examples 6 to 10, the performance of the organic light-emitting device was evaluated in the same manner as in Experimental Example 2, and the results are shown in Table 4 below.

[0212] Table 4

[0213]

[0214]

[0215] The compounds of the present invention are characterized by containing the following units, which are bonded to each other in the form of aromatic amines. The first unit is a direct bond between a benzene containing a heteroaryl group represented by Chemical Formula B and a phenanthrene represented by Chemical Formula A, and the second unit is a heteroaryl group containing X2 represented by Chemical Formula D or Chemical Formula E. In addition, the compounds of the present invention are formed by the phenanthrene group represented by Chemical Formula A and the nitrogen atom (N) of Chemical Formula C being in the meta or para position relative to the ring containing X1 represented by Chemical Formula B. Comparative Compound A (Comparative Examples 1 and 6) differs from the second unit of the present invention in that the heteroaryl group containing X2 is absent. For Comparative Compounds B, C, and D, unlike the first unit of the present invention, the benzene containing a heteroaryl group containing X1 is bonded to a phenyl or naphthyl group. In addition, for Comparative Compound E, the phenanthrene group of Chemical Formula A is bonded to position 4 of Chemical Formula B, and the aromatic amine nitrogen unit of Chemical Formula C is bonded to position 3 of Chemical Formula B, which is an ortho position. It can be seen from Table 3 and Table 4 that, compared with the organic light-emitting devices using the comparative compounds A to E, the organic light-emitting devices using the compounds of the present invention have much better device performance.

[0216] The preferred embodiments of the present invention are described in detail above, but the scope of the present invention is not limited thereto. Various modifications and improvements made by ordinary technicians in the technical field of the present invention using the basic concepts of the present invention defined in the following claims also fall within the scope of the present invention.

Claims

1. An organic compound represented by the following chemical formula 1, [Chemical Formula 1] in, X1 is oxygen or sulfur, m is an integer from 0 to 9, n is an integer from 0 to 6, L1 and L2 are the same as or different from each other, and are each independently selected from the group consisting of a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylene group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms, and a substituted or unsubstituted heteroarylalkylene group having 6 to 60 carbon atoms, Ar1 is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, Ar2 is an oxygen-containing or sulfur-containing substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, R1 and R2 are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms. The substituents of L1, L2, Ar1, Ar2, R1 and R2 are each independently selected from deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, trimethylsilyl, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, alkenyl having 2 to 30 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, alkynyl having 2 to 30 carbon atoms, cycloalkynyl having 3 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, heteroaryl having 5 to 60 carbon atoms, heteroaralkyl having 6 to 60 carbon atoms, At least one selected from the group consisting of an amino group, an alkylamino group having 1 to 30 carbon atoms, an arylalkylamino group having 7 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 5 to 60 carbon atoms, a silyl group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, and an arylthio group having 6 to 30 carbon atoms; when the group has a plurality of such substituents, the substituents may be the same as or different from each other.

2. The organic compound according to claim 1, wherein The chemical formula 1 is an organic compound represented by the following chemical formula 2 or chemical formula 3, [Chemical Formula 2] [Chemical Formula 3] In the Chemical Formula 2 or Chemical Formula 3, m, n and X1 are as defined in Chemical Formula 1, L1, L2, Ar1, R1 and R2 and their substituents have the same meanings as those defined in Chemical Formula 1. X2 is oxygen or sulfur, o1 is an integer from 0 to 7, o2 is an integer from 0 to 5, R3 are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms. The substituents for R3 are each independently selected from the group consisting of deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxy, trimethylsilyl, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, alkenyl having 2 to 30 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, alkynyl having 2 to 30 carbon atoms, cycloalkynyl having 3 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, heteroaryl having 5 to 60 carbon atoms, heteroaralkyl having 6 to 60 carbon atoms, amino, 1 to 30 carbon atoms, 1 to 20 carbon atoms, 2 to 30 carbon atoms, 3 to 20 carbon atoms, 4 to 5 carbon atoms, 6 to 60 carbon atoms, 6 to 60 carbon atoms, 1 to 20 carbon atoms, 2 to 30 carbon atoms, 3 to 20 carbon atoms, 4 to 5 carbon atoms, 6 to 60 carbon atoms, 6 to 60 carbon atoms, 6 to 60 carbon atoms, 6 to 60 carbon atoms, 6 to 7 ... The present invention further comprises at least one of the group consisting of an alkylamino group having 1 to 30 carbon atoms, an arylalkylamino group having 7 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 5 to 60 carbon atoms, a silyl group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, and an arylthio group having 6 to 30 carbon atoms; when the present invention has a plurality of such substituents, the substituents may be the same as or different from each other.

3. The organic compound according to claim 1 or 2, wherein In Chemical Formula 1, Chemical Formula 2, and Chemical Formula 3, the phenanthryl group and the nitrogen atom N are in the meta position or the para position relative to each other based on the ring including X1.

4. An organic light-emitting device, in, include: a first electrode; a second electrode, opposite to the first electrode; and One or more organic layers are disposed between the first electrode and the second electrode, At least one of the one or more organic layers is an organic layer containing the organic compound according to claim 1 .

5. The organic light-emitting device according to claim 4, in, The organic layer comprising the organic compound according to claim 1 is a hole transport layer or a hole transport auxiliary layer. The organic light-emitting device according to claim 5 , wherein: The organic layer further includes at least one selected from the group consisting of a hole injection layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

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