Organic compound and organic light-emitting device comprising same

Abstract

The purpose of the present invention is to provide a novel organic compound and an organic light-emitting device comprising same. An organic light-emitting device comprising the compound represented by chemical formula 1 of the present invention has excellent driving voltage, luminous efficiency, external quantum efficiency (EQE) and stability and a long lifespan.

Description

Organic compounds and organic light-emitting devices containing the same

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

[0002] Organic light-emitting diodes (OLEDs) have a simpler structure than other flat panel displays such as liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), and have various advantages in manufacturing processes. They also have high brightness and excellent viewing angle characteristics, a fast response speed, and low driving voltage. Therefore, they are being actively developed and commercialized for use as light sources for flat panel displays such as wall-mounted TVs, backlights for displays, lighting, and billboards.

[0003] Organic light-emitting diodes (OLEDs) consist of an organic layer sandwiched between two electrodes. These devices utilize the principle that electrons and holes are injected into the light-emitting layer from the two electrodes, generating excitons through the combination of electrons and holes, and emitting light when the generated excitons drop from the excited state to the ground state.

[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 having different peak wavelengths, thereby enabling a specific color to be realized through a combination of light having different peak wavelengths.

[0005] These organic light-emitting devices can be divided into top-emitting and bottom-emitting devices. Top-emitting devices use a reflective cathode to emit light generated in the light-emitting layer toward a translucent anode. Conversely, bottom-emitting devices use a reflective anode to emit light generated in the light-emitting layer and reflected by the anode toward a transparent cathode toward the driving thin-film transistor.

[0006] Meanwhile, the biggest issues for organic electroluminescent devices are their lifespan and efficiency. As displays become larger, these efficiency and lifespan issues must be resolved. In organic electroluminescent devices, the characteristics of the components contained in each layer of the organic film layer, which is composed of one or more layers including a light-emitting layer between the anode and cathode, affect the driving voltage, luminous efficiency, and brightness of the device, and these characteristics have a significant impact on the device's lifespan.

[0007] Accordingly, research on the components contained in each layer of the organic film layer is being actively conducted.

[0008] The purpose of the present invention is to provide a novel organic compound and an organic light-emitting device comprising the same.

[0009] In addition to the above-mentioned tasks, embodiments according to the present invention can be used to achieve other tasks not specifically mentioned.

[0010] The present invention is not limited to the purposes mentioned above, and other purposes and advantages of the present invention that are not mentioned can be understood by the following description and will be more clearly understood by the embodiments of the present invention.

[0011] In addition, it will be readily apparent that the objects and advantages of the present invention can be realized by the means and combinations thereof set forth in the claims.

[0012] In order to solve the above problem, according to one embodiment of the present invention, an organic compound having a novel structure represented by the following chemical formula 1 can be provided, and the definition of the following chemical formula 1 is the same as that described in the present specification and claims.

[0013] [Chemical Formula 1]

[0014]

[0015] According to another embodiment of the present invention, an organic light-emitting device may be provided, which may include a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer may include an electron transport layer and / or an electron transport auxiliary layer, and includes an organic compound represented by the chemical formula 1 of the present invention.

[0016] The organic compound represented by the chemical formula 1 of the present invention can exhibit excellent electron transport properties.

[0017] In addition, at least one of the electron transport layer and the electron transport auxiliary layer of the organic light-emitting device of the present invention includes an organic compound represented by the chemical formula 1 of the present invention, thereby improving the driving voltage, efficiency, and lifespan characteristics of the organic light-emitting device.

[0018] In addition, the organic light-emitting device of the present invention can excellently implement the color coordinates targeted by the light-emitting layer even when the electron transport layer and / or electron transport auxiliary layer including the organic compound represented by the chemical formula 1 of the present invention is combined with a light-emitting layer of any color.

[0019] The effects of this specification are not limited to the effects mentioned above, and other effects not mentioned will be clearly understood by those skilled in the art from the description below.

[0020] The above effects and additional effects are described in detail below.

[0021] The above-described objects, features and advantages are described in detail below, and accordingly, the above-described objects, features and advantages in the technical field to which the present invention belongs are described in detail below, and accordingly, a person having ordinary knowledge in the technical field to which the present invention belongs can easily implement the technical idea of ​​the present invention.

[0022] In describing this specification, if it is determined that a detailed description of a related known technology may unnecessarily obscure the gist of this specification, the detailed description is omitted.

[0023] In this specification, when a component is described as “including,” “having,” “consisting of,” “arranged,” or “equipped,” other parts may be added unless “only” is used. When a component is described as singular, it includes the plural unless otherwise explicitly stated.

[0024] In interpreting the components in this specification, even if there is no separate explicit description, it is interpreted to include the range of error.

[0025] In this specification, the phrase “any component is disposed on (or below)” a component or “on (or below)” a component may mean not only that any component is disposed in contact with the upper surface (or lower surface) of the component, but also that other components may be interposed between the component and any component disposed on (or below) the component.

[0026] The term “halogen group” as used herein includes fluorine, chlorine, bromine and iodine.

[0027] The term “alkyl group” as used herein refers to both straight-chain alkyl radicals and branched-chain alkyl radicals. Unless specifically defined, an alkyl group contains 1 to 30 carbon atoms and may include, but is not limited to, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isoamyl, hexyl, and the like. Additionally, an alkyl group may be optionally substituted.

[0028] The term “cycloalkyl group” as used herein refers to a cyclic alkyl radical. Unless otherwise specified, a cycloalkyl group contains 3 to 20 carbon atoms and may include, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like. Additionally, a cycloalkyl group may be optionally substituted.

[0029] The term “alkenyl group” as used herein refers to both straight-chain alkene radicals and branched-chain alkene radicals having at least one carbon-carbon double bond. Unless otherwise specified, an alkenyl group contains 2 to 30 carbon atoms and may include, but is not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like. Additionally, an alkenyl group may be optionally substituted.

[0030] The term “cycloalkenyl group” as used herein refers to a cyclic alkenyl radical. Unless otherwise specified, a cycloalkenyl group contains 3 to 20 carbon atoms, and further, the cycloalkenyl group may be optionally substituted.

[0031] The term “alkynyl group” as used herein refers to both straight-chain alkyne radicals and branched-chain alkyne radicals having at least one carbon-carbon triple bond. Unless otherwise specified, an alkynyl group contains 2 to 30 carbon atoms. It may include, but is not limited to, ethynyl, 2-propynyl, and the like. Additionally, an alkynyl group may be optionally substituted.

[0032] The term “cycloalkynyl group” as used herein refers to a cyclic alkynyl radical. Unless otherwise specified, a cycloalkynyl group contains 3 to 20 carbon atoms, and further, the cycloalkynyl group may be optionally substituted.

[0033] The terms “aralkyl group” or “arylalkyl group” used herein are used interchangeably and mean an alkyl group having an aromatic group as a substituent, and further, the aralkyl group (arylalkyl group) may be optionally substituted.

[0034] The terms “aryl group” or “aromatic group” as used herein are used interchangeably, and an aryl group includes both a single ring group and a polycyclic ring group. A polycyclic ring may include a “fused ring,” which is two or more rings in which two carbon atoms are common to two adjacent rings. It may also include a form in which two or more rings are simply attached to each other or fused. Unless otherwise specified, an aryl group contains 6 to 30 carbon atoms, and may include, but is not limited to, phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, and the like. In addition, an aryl group may be optionally substituted.

[0035] The terms “heteroaryl group” or “heteroaromatic group” as used herein are used interchangeably, and heteroaryl groups include both monocyclic groups and polycyclic groups. Polycyclic rings may include “fused rings,” which are two or more rings in which two carbons or heteroatoms are common to two adjacent rings. In addition, it may also include a form in which two or more rings are simply attached to each other or fused. Unless otherwise specified, a heteroaryl group contains 5 to 60 carbon atoms, and when there are 1 or 2 carbon atoms, it may include an additional heteroatom to form a ring. In addition, the heteroaryl group may contain 1 to 30 carbon atoms, wherein at least one carbon in the ring is substituted with a heteroatom such as oxygen (O), nitrogen (N), sulfur (S), or selenium (Se), and may be a 6-membered monocyclic ring such as pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, a polycyclic ring such as phenoxathinyl, indolizinyl, indolyl, purinyl, quinolyl, isoquinolyl, benzoxyzolyl, benzothiazolyl, dibenzoxyzolyl, dibenzothiazolyl, benzimidazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, phenylcarbazolyl, 9-phenylcarbazolyl, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl. It may include, but is not limited to, 2-pyridinyl, 2-pyrimidinyl, etc. Additionally, the heteroaryl group may be optionally substituted.

[0036] The term “heterocyclic group” used herein means a group in which at least one of the carbon atoms constituting an aryl group, a cycloalkyl group, a cycloalkenyl group, a cycloalkynyl group, an arylalkyl group, an arylamino group, etc. is substituted with a heteroatom such as oxygen (O), nitrogen (N), or sulfur (S), and with reference to the above definition, includes a heteroaryl group, a heterocycloalkyl group, a heterocycloalkenyl group, a heterocycloalkynyl group, a heteroarylalkyl group, a heteroarylamino group, etc., and further, the heterocycle may be optionally substituted.

[0037] The term “carbon ring” used in this specification may be used as a term including both “cycloalkyl group”, which is an alicyclic ring group, and “aryl group (aromatic group)”, which is an aromatic ring group, unless there is a special limitation.

[0038] The terms “heteroalkyl group” and “heteroarylalkyl group” used herein mean that at least one of the carbon atoms constituting the alkyl group and arylalkyl group is substituted with a heteroatom such as oxygen (O), nitrogen (N), sulfur (S), or selenium (Se), and further, the heteroalkyl group and heteroarylalkyl group may be optionally substituted.

[0039] The terms “alkylamino group,” “arylalkylamino group,” “arylamino group,” and “heteroarylamino group” used in this specification mean an amino group (or amine group) substituted with the alkyl group, arylalkyl group, aryl group, or heteroaryl group, and include all primary, secondary, and tertiary amino groups (or amine groups), and additionally, the alkylamino group, arylalkylamino group, arylamino group, and heteroarylamino group may be optionally substituted.

[0040] The terms “alkylsilyl group,” “arylsilyl group,” “alkoxy group,” “aryloxy group,” “alkylthio group,” and “arylthio group” used in this specification mean that the silyl group, oxy group, and thio group are substituted with the alkyl group and aryl group, respectively, and additionally, the alkylsilyl group, arylsilyl group, alkoxy group, aryloxy group, alkylthio group, and arylthio group may be optionally substituted.

[0041] The terms “arylene group,” “arylalkylene group,” “heteroarylene group,” and “heteroarylalkylene group” as used herein mean that each of the aryl group, arylalkyl group, heteroaryl group, and heteroarylalkyl group is a divalent substituent that further includes one substitution. Additionally, the arylene group, arylalkylene group, heteroarylene group, and heteroarylalkylene group may be optionally substituted.

[0042] The term “substitution” as used herein means that a hydrogen (H) atom bonded to a carbon or nitrogen atom of the compound of the present invention is replaced with a substituent other than hydrogen, and when there are multiple substituents, each substituent may be the same or different from each other.

[0043] The above substituents are each independently selected from the group consisting of deuterium, trifluoromethyl, nitro, halogen, hydroxy, trimethylsilyl (TMS), alkyl group having 1 to 30 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, alkenyl group having 2 to 30 carbon atoms, cycloalkenyl group having 3 to 20 carbon atoms, alkynyl group having 2 to 30 carbon atoms, cycloalkynyl group having 3 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, heteroaryl group having 5 to 60 carbon atoms, heteroarylalkyl group having 6 to 60 carbon atoms, amine group, alkylamino group having 1 to 30 carbon atoms, arylalkylamino group having 7 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, and 5 to 60 carbon atoms. It is substituted with one or more substituents selected from the group consisting of a heteroarylamino group, 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, and when substituted with multiple substituents, they are the same as or different from each other, and can combine with adjacent groups to form a substituted or unsubstituted ring.

[0044] Each target and substituent defined in this specification may be the same or different unless otherwise specified.

[0045] Hereinafter, the organic compound according to the present invention and the organic light-emitting device including the same will be described in detail.

[0046] The organic compound of the present invention can be expressed by the following chemical formula 1.

[0047] [Chemical Formula 1]

[0048]

[0049] X is oxygen (O) or sulfur (S),

[0050] Y1, Y2 and Y3 are nitrogen (N) or CR2,

[0051] At least two of Y1, Y2 and Y3 are nitrogen (N),

[0052] Z1, Z2 and Z3 are nitrogen (N) or CR3,

[0053] L1 and L2 are the same 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,

[0054] A is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 6 to 60 carbon atoms, an 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, and can combine with adjacent groups to form a substituted or unsubstituted ring,

[0055] Ar1 and Ar2 are the same or different from each other, and are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl 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, and can combine with adjacent groups to form a substituted or unsubstituted ring.

[0056] R1, R2 and R3 are the same or different, 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 arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl 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, and can combine with adjacent groups to form a substituted or unsubstituted ring.

[0057] p is an integer from 0 to 7,

[0058] The substituents of L1, L2, A, Ar1, Ar2, R1, R2 and R3 are each independently deuterium, trifluoromethyl group, nitro group, halogen group, hydroxy group, trimethylsilyl group (TMS), alkyl group having 1 to 30 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, alkenyl group having 2 to 30 carbon atoms, cycloalkenyl group having 3 to 20 carbon atoms, alkynyl group having 2 to 30 carbon atoms, cycloalkynyl group having 3 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, heteroaryl group having 5 to 60 carbon atoms, heteroarylalkyl group having 6 to 60 carbon atoms, amine group, alkylamino group having 1 to 30 carbon atoms, arylalkylamino group having 7 to 30 carbon atoms, 6 carbon atoms It is substituted with one or more substituents selected from the group consisting of an arylamino 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, and when substituted with multiple substituents, they are the same as or different from each other, and can combine with adjacent groups to form a substituted or unsubstituted ring.

[0059] According to an embodiment of the present invention, the direct bond or single bond means that components of the chemical formula on both sides are directly bonded, such as in the case where L1 and L2 are absent in the chemical formula.

[0060] According to an embodiment of the present invention, L1 and L2 are the same as or different from each other, and can each independently be a direct bond or a divalent phenylene group.

[0061] The above direct bond means that the components of both chemical formulas are directly bonded based on L1 and L2, such as in the absence of L1 and L2 in Chemical Formula 1. This can be confirmed by Chemical Formula 2-1, etc.

[0062] The above divalent phenylene group means that two positions are substituted in a six-position phenylene group capable of substitution bonding. This can be any one of 1,2 (ortho) substitution, 1,3 (meta) substitution, and 1,4 (para) substitution, and can be selected from the structures below. (In the following partial compounds, * means a part where the partial compound is bonded by a single bond.)

[0063]

[0064] According to an embodiment of the present invention, Y1, Y2 and Y3 may be as follows.

[0065] - Y1 and Y2 are nitrogen, Y3 is CR2, and R2 is hydrogen

[0066] - Y1 and Y3 are nitrogen, Y2 is CR2, and R2 is hydrogen

[0067] - Y2 and Y3 are nitrogen, Y1 is CR1, and R1 is hydrogen

[0068] - Y1, Y2 and Y3 are all nitrogen

[0069] According to an embodiment of the present invention, A may be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0070] According to an embodiment of the present invention, A may be substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl.

[0071] According to an embodiment of the present invention, Ar1 and Ar2 may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl.

[0072] According to an embodiment of the present invention, the compound of the above chemical formula 1 may contain at least one deuterium.

[0073] According to an embodiment of the present invention, the organic compound of the chemical formula 1 can be expressed by the following chemical formula 2.

[0074] [Chemical Formula 2]

[0075]

[0076] Here, X, L1, L2, A, Ar1, Ar2, R1 and R2 and their substituents are as defined in the above chemical formula 1.

[0077] According to an embodiment of the present invention, the organic compounds of the chemical formulae 1 and 2 can be expressed by the following chemical formulae 2-1 to 2-8.

[0078] In the following chemical formulas 2-1 to 2-8, 2-1-1 to 2-1-4, 2-2-1 to 2-2-4, 2-3-1 to 2-3-6, 2-4-1 to 2-4-6, 2-5-1 to 2-5-4, 2-6-1 to 2-6-4, 2-7-1 to 2-7-6, 2-8-1 to 2-8-6, X, A, Ar1, Ar2, R1, R2 and p, the substituents thereof are as defined in the above chemical formula 1.

[0079] [Chemical Formula 2-1]

[0080]

[0081] The above 2-1 structure may include, but is not limited to, the following structures.

[0082]

[0083] [Chemical Formula 2-2]

[0084]

[0085] The above 2-2 structure may include, but is not limited to, the following structures.

[0086]

[0087] [Chemical Formula 2-3]

[0088]

[0089] The above 2-3 structures may include, but are not limited to, the following structures.

[0090]

[0091] [Chemical Formula 2-4]

[0092]

[0093] The above 2-4 structures may include, but are not limited to, the following structures.

[0094]

[0095] [Chemical Formula 2-5]

[0096]

[0097] The above 2-5 structures may include, but are not limited to, the following structures.

[0098]

[0099] [Chemical Formula 2-6]

[0100]

[0101] The above 2-6 structures may include, but are not limited to, the following structures.

[0102]

[0103] [Chemical Formula 2-7]

[0104]

[0105] The above 2-7 structure may include, but is not limited to, the following structures.

[0106]

[0107] [Chemical Formula 2-8]

[0108]

[0109] The above 2-8 structure may include, but is not limited to, the following structures.

[0110]

[0111] According to an embodiment of the present invention, the organic compound of the chemical formula 1 can be expressed by the following chemical formula 3.

[0112] [Chemical Formula 3]

[0113]

[0114] Here, X, L1, L2, A, Ar1, Ar2, R1 and R2 and their substituents are as defined in the above chemical formula 1.

[0115] According to an embodiment of the present invention, the organic compounds of the chemical formulae 1 and 3 can be expressed by the following chemical formulae 3-1 to 3-8.

[0116] In the following chemical formulas 3-1 to 3-8, 3-1-1 to 3-1-4, 3-2-1 to 3-2-4, 3-3-1 to 3-3-6, 3-4-1 to 3-4-6, 3-5-1 to 3-5-4, 3-6-1 to 3-6-4, 3-7-1 to 3-7-6, 3-8-1 to 3-8-6, X, A, Ar1, Ar2, R1, R2 and p, the substituents thereof are as defined in the above chemical formula 1.

[0117] [Chemical Formula 3-1]

[0118]

[0119] The above 3-1 structure may include, but is not limited to, the following structures.

[0120]

[0121] [Chemical Formula 3-2]

[0122]

[0123] The above 3-2 structure may include, but is not limited to, the following structures.

[0124]

[0125] [Chemical Formula 3-3]

[0126]

[0127] The above 3-3 structure may include, but is not limited to, the following structures.

[0128]

[0129] [Chemical Formula 3-4]

[0130]

[0131] The above 3-4 structures may include, but are not limited to, the following structures.

[0132]

[0133] [Chemical Formula 3-5]

[0134]

[0135] The above 3-5 structures may include, but are not limited to, the following structures.

[0136]

[0137] [Chemical Formula 3-6]

[0138]

[0139] The above 3-6 structures may include, but are not limited to, the following structures.

[0140]

[0141] [Chemical Formula 3-7]

[0142]

[0143] The above 3-7 structure may include, but is not limited to, the following structures.

[0144]

[0145] [Chemical Formula 3-8]

[0146]

[0147] The above 3-8 structure may include, but is not limited to, the following structures.

[0148]

[0149] According to an embodiment of the present invention, the organic compound of the chemical formula 1 can be expressed by the following chemical formula 4.

[0150] [Chemical Formula 4]

[0151]

[0152] Here, X, L1, L2, A, Ar1, Ar2, R1 and R2 and their substituents are as defined in the above chemical formula 1.

[0153] According to an embodiment of the present invention, the organic compounds of the chemical formulae 1 and 4 can be expressed by the following chemical formulae 4-1 to 4-8.

[0154] In the following chemical formulas 4-1 to 4-8, 4-1-1 to 4-1-4, 4-2-1 to 4-2-4, 4-3-1 to 4-3-6, 4-4-1 to 4-4-6, 4-5-1 to 4-5-4, 4-6-1 to 4-6-4, 4-7-1 to 4-7-6, 4-8-1 to 4-8-6, X, A, Ar1, Ar2, R1, R2 and p, the substituents thereof are as defined in the above chemical formula 1.

[0155] [Chemical Formula 4-1]

[0156]

[0157] The above 4-1 structure may include, but is not limited to, the following structures.

[0158]

[0159] [Chemical Formula 4-2]

[0160]

[0161] The above 4-2 structure may include, but is not limited to, the following structures.

[0162]

[0163] [Chemical Formula 4-3]

[0164]

[0165] The above 4-3 structure may include, but is not limited to, the following structures.

[0166]

[0167] [Chemical Formula 4-4]

[0168]

[0169] The above 4-4 structure may include, but is not limited to, the following structures.

[0170]

[0171] [Chemical Formula 4-5]

[0172]

[0173] The above 4-5 structures may include, but are not limited to, the following structures.

[0174]

[0175] [Chemical Formula 4-6]

[0176]

[0177] The above 4-6 structures may include, but are not limited to, the following structures.

[0178]

[0179] [Chemical Formula 4-7]

[0180]

[0181] The above 4-7 structures may include, but are not limited to, the following structures.

[0182]

[0183] [Chemical Formula 4-8]

[0184]

[0185] The above 4-8 structures may include, but are not limited to, the following structures.

[0186]

[0187] According to one embodiment of the present invention, in Chemical Formula 1, Chemical Formula 2, Chemical Formula 2-1, Chemical Formula 2-2, Chemical Formula 2-3, Chemical Formula 2-4, Chemical Formula 2-5, Chemical Formula 2-6, Chemical Formula 2-7, Chemical Formula 2-8, Chemical Formula 3, Chemical Formula 3-1, Chemical Formula 3-2, Chemical Formula 3-3, Chemical Formula 3-4, Chemical Formula 3-5, Chemical Formula 3-6, Chemical Formula 3-7, Chemical Formula 3-8, Chemical Formula 4, Chemical Formula 4-1, Chemical Formula 4-2, Chemical Formula 4-3, Chemical Formula 4-4, Chemical Formula 4-5, Chemical Formula 4-6, Chemical Formula 4-7, Chemical Formula 4-8, L1 and L2 may be selected from compounds having structures A1 to A6 below. (In the partial compounds below, * indicates a part in which the partial compounds are bonded by a single bond.)

[0188]

[0189] According to one embodiment of the present invention, in Chemical Formula 1, Chemical Formula 2, Chemical Formula 2-1, Chemical Formula 2-2, Chemical Formula 2-3, Chemical Formula 2-4, Chemical Formula 2-5, Chemical Formula 2-6, Chemical Formula 2-7, Chemical Formula 2-8, Chemical Formula 3, Chemical Formula 3-1, Chemical Formula 3-2, Chemical Formula 3-3, Chemical Formula 3-4, Chemical Formula 3-5, Chemical Formula 3-6, Chemical Formula 3-7, Chemical Formula 3-8, Chemical Formula 4, Chemical Formula 4-1, Chemical Formula 4-2, Chemical Formula 4-3, Chemical Formula 4-4, Chemical Formula 4-5, Chemical Formula 4-6, Chemical Formula 4-7, Chemical Formula 4-8, A may be selected from compounds having structures B1 to B18 below. (In the following partial compounds, * indicates a part in which the partial compound is bonded by a single bond.)

[0190]

[0191]

[0192] According to one embodiment of the present invention, in Chemical Formula 1, Chemical Formula 2, Chemical Formula 2-1, Chemical Formula 2-2, Chemical Formula 2-3, Chemical Formula 2-4, Chemical Formula 2-5, Chemical Formula 2-6, Chemical Formula 2-7, Chemical Formula 2-8, Chemical Formula 3, Chemical Formula 3-1, Chemical Formula 3-2, Chemical Formula 3-3, Chemical Formula 3-4, Chemical Formula 3-5, Chemical Formula 3-6, Chemical Formula 3-7, Chemical Formula 3-8, Chemical Formula 4, Chemical Formula 4-1, Chemical Formula 4-2, Chemical Formula 4-3, Chemical Formula 4-4, Chemical Formula 4-5, Chemical Formula 4-6, Chemical Formula 4-7, Chemical Formula 4-8, Ar1 and Ar2 may be selected from compounds having structures M1 to M32 below. (In the partial compounds below, * indicates a part in which the partial compounds are bonded by a single bond.)

[0193]

[0194]

[0195] According to one embodiment of the present invention, the compound represented by Chemical Formula 1 may be selected from the group consisting of structures 1 to 82, tables 1 to 24, and deuterium compound structures 1919 to 1927, but is not limited thereto.

[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] The organic light-emitting device of the present invention comprises a first electrode, a second electrode facing the first electrode, and one or more organic layers positioned on the inner side of the first electrode and the second electrode, and at least one of the organic layers may comprise a compound represented by the chemical formula 1.

[0225] The above organic light-emitting device may include at least one layer of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, or an electron injection layer as an organic layer, and may additionally include a charge generation layer, a hole transport auxiliary layer, a light-emitting auxiliary layer, an electron transport auxiliary layer, etc.

[0226] For example, the organic light-emitting device may have a structure in which a first electrode (anode), a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emitting layer (EML), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), and a second electrode (cathode) are sequentially stacked.

[0227] An organic light-emitting device according to an embodiment of the present invention may include an electron transport layer or an electron transport auxiliary layer including a compound represented by chemical formula 1.

[0228] The organic light-emitting device according to the above embodiment of the present invention may further include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection layer.

[0229] For example, the first electrode may include a transparent and highly conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO).

[0230] The above hole injection layer or hole transport layer compound is not particularly limited, and any compound that is typically used as a hole injection layer or hole transport layer compound may be used. Non-limiting examples of the hole injection layer or hole transport layer compound may include phthalocyanine derivatives, porphyrin derivatives, triarylamine derivatives, and indolocarbazole derivatives. For example, 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (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"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA), N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-di(naphthalen-1-yl)-N,N'-biphenyl-benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD).

[0231] The compound included in the above-mentioned light-emitting layer is not particularly limited, and any compound that is typically used as a light-emitting layer compound may be used. A single light-emitting compound or a light-emitting host compound may be used.

[0232] The luminescent compound of the above-mentioned luminescent layer includes, but is not limited to, a compound capable of causing luminescence through phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes. The luminescent compound can be selected from a variety of materials depending on the desired luminescent color. Non-limiting examples of luminescent compounds include condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bistyryl derivatives, bistyrylarylene derivatives, diazindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives, dibenzofuran derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthenes Examples thereof include derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violantrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, benzofluorene derivatives, aromatic boron derivatives, aromatic nitrogen boron derivatives, and metal complexes (complexes of metals such as Ir, Pt, Au, Eu, Ru, Re, Ag, and Cu and heteroaromatic ring ligands, 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-boranaphtho[3,2,1-de]anthracene (t-DABNA-dtB), PtOEP, Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), 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(piq)2(acac), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·(PF6)2, Ir(BT)2(acac), Ir(DMP)3, Ir(Mphq)3, Ir(phq)2tpy, fac-Ir(ppy)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, Includes FIrpic, etc.

[0233] As the host compound of the above-mentioned light-emitting layer, a light-emitting host, a hole-transporting host, an electron-transporting host, or a combination thereof can be used. Non-limiting examples of light-emitting host compounds include condensed ring derivatives such as anthracene or pyrene, bisstyryl derivatives such as bisstyrylanthracene derivatives or distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, N-phenylcarbazole derivatives, carbazonitrile derivatives, and the like. Non-limiting examples of hole-transporting host materials include carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, triarylamine derivatives, indolocarbazole derivatives, and benzoxazinophenoxazine derivatives. Non-limiting examples of electron-transporting host materials include pyridine derivatives, triazine derivatives, phosphine oxide derivatives, benzofuropyridine derivatives, and dibenzoxacillin derivatives. For example, it includes 9,10-bis(2-naphthyl)anthracene (ADN), tris(8-hydroxyquinolinato)aluminum (Alq3), BAlq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis(2,2-biphenylethenyl)-1,1'-biphenyl) series, spiro-DPVBi (spiro-4,4'-bis(2,2-biphenylethenyl)-1,1'-biphenyl), LiPBO (2-(2-benzooxazolyl)-phenol lithium salt), bis(biphenylvinyl)benzene, aluminum-quinoline metal complexes, imidazole, thiazole, and oxazole metal complexes, etc.

[0234] An electron blocking layer (EBL) may be formed between the hole transport layer and the light emitting layer. The electron blocking layer compound is not particularly limited, and any compound commonly used as an electron blocking layer compound may be used. For example, the electron blocking layer may include N-phenyl-N-(4-(spiro[benzo[d,e]anthracen-7,9'-fluoren]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine).

[0235] An electron transport auxiliary layer may be formed between the above-described light-emitting layer and the electron transport layer. The electron transport auxiliary layer compound is not particularly limited, and any compound that is typically used as an electron transport auxiliary layer compound may be used. For example, the electron transport auxiliary layer may include 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine, etc.

[0236] The above electron injection layer, electron transport layer, electron transport auxiliary layer or hole blocking layer compound is not particularly limited, and any compound that is typically used as an electron injection layer, electron transport layer, electron transport auxiliary layer or hole blocking layer compound may be used. Non-limiting examples of electron injection layer or electron transport layer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives, imidazopyridine derivatives, borane derivatives, benzoimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives, Examples thereof include naphthyridine derivatives, aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, quinolinol-based metal complexes, hydroxyazole-based metal complexes, azomethine-based metal complexes, tropolone-based metal complexes, flavonol-based metal complexes, benzoquinoline-based metal complexes, and metal salts. These materials can be used alone, but they can also be mixed with other materials. For example, they can include substances such as 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, tris(8-hydroxyquinolinato)aluminum (Alq3), LiF, Liq, Li2O, BaO, NaCl, and CsF.

[0237] The above second electrode (cathode) may include a material such as lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). In addition, in the case of a top-emitting organic light-emitting device, a transparent cathode through which light can pass may be formed using indium tin oxide (ITO) or indium zinc oxide (IZO).

[0238] The organic light-emitting device according to an embodiment of the present invention may be a front-emitting device or a back-emitting device.

[0239] An organic light-emitting device according to an embodiment of the present invention can be used in a display device.

[0240] The organic light-emitting device according to an embodiment of the present invention can be applied to, but is not limited to, transparent display devices, mobile display devices, flexible display devices, etc.

[0241] Hereinafter, the synthesis method of the above compounds is described using representative examples. However, the synthesis method of the compounds of the present invention is not limited to the methods exemplified below.

[0242] X, Y1, Y2, Y3, L1, L2, A, Ar1, Ar2, R1 and R2 described in SUB 1, SUB 2, SUB 3, SUB 4, Product below are as defined in the chemical formula 1 above.

[0243] In the reaction formula below, Halogen refers to a halogen group, but any equivalent halogen group is possible.

[0244] In the following reaction formula, boronic compound refers to boronic acid, boronic ester, dioxaborolane, etc., but any equivalent boronic compound is possible.

[0245] In the following reaction formula, the solvent, catalyst, etc. are representative examples, and all equivalent solvents, catalysts, etc. are possible.

[0246] [Synthesis example]

[0247] 1. Synthesis of SUB 3

[0248] SUB 3 can be synthesized as follows, but is not limited thereto.

[0249] [Reaction Formula 1]

[0250]

[0251] Under a nitrogen atmosphere, SUB 1 (44 mmol, 5.4 g), SUB 2 (40 mmol, 21.7 g), K2CO3 (120 mmol, 16.6 g), Pd(PPh3)4 (1.6 mmol, 4.6 g), 1,4-Dioxane (440 mL), and water (88 mL) were added to a 1000 mL flask and stirred under reflux conditions for 24 hours. After completion of the reaction, the organic layer was extracted using CH2Cl2 and water. The extracted solution was treated with MgSO4 to remove residual moisture, concentrated under reduced pressure, and purified using column chromatography, followed by recrystallization to obtain 19.4 g of the following SUB 3-6 (Yield: 90%). m / z=538.10 (C34H23BrN2=539.48)

[0252] Representatively synthesized SUB 3 compounds are shown in Table 25 below, and SUB 3 compounds for the specific compounds of the present invention and similar compounds can be synthesized by referring to the above synthesis examples.

[0253]

[0254]

[0255]

[0256] 2. Product synthesis

[0257] The Product can be synthesized as follows, but is not limited thereto.

[0258] [Reaction Formula 2]

[0259]

[0260] Under a nitrogen atmosphere, SUB 3 (20 mmol, 10.8 g), SUB 4 (22 mmol, 5.4 g), K2CO3 (60 mmol, 8.3 g), Pd(PPh3)4 (0.8 mmol, 0.9 g), 1,4-Dioxane (110 mL), and water (22 mL) were added to a 250 mL flask and stirred under reflux conditions for 24 hours. After completion of the reaction, the organic layer was extracted using CH2Cl2 and water. The extracted solution was treated with MgSO4 to remove residual moisture, concentrated under reduced pressure, and purified using column chromatography, followed by recrystallization to obtain 9.8 g of compound 2 as a product. (Yield: 78%) m / z=626.24 (C34H23BrN2=626.76)

[0261] Representative synthesized compounds are shown in Table 26 below, and the specific compounds of the present invention and similar compounds can be synthesized with reference to the above synthetic examples.

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269] [Experimental Example 1] Simulation Results

[0270] Experimental Example 1: Electron Transport Auxiliary Layer Simulation Results

[0271] The electron transport auxiliary layer plays a role in preventing holes from leaking to the light-emitting layer interface due to the difference in LUMO levels between the electron transport layer and the light-emitting layer. To this end, it is preferable that the LUMO energy difference with the light-emitting layer be greater than the LUMO energy difference with the electron transport layer.

[0272]

[0273] Experimental Example 2: Electron Transport Layer Simulation Results

[0274] The electron transport layer has an appropriate LUMO level between the electron transport auxiliary layer and the electron injection layer or between the emitting layer (if there is no electron transport auxiliary layer) and the electron injection layer, thereby allowing electrons to be transferred to the electron transport auxiliary layer or the emitting layer (if there is no electron transport auxiliary layer). To this end, it is preferable that the LUMO energy difference between the electron transport auxiliary layer or the emitting layer (if there is no electron transport auxiliary layer) be smaller than the LUMO energy difference between the electron injection layer and the electron transport auxiliary layer.

[0275]

[0276] [Experimental Example 3] Electron Transport Auxiliary Layer Device Experiment Results

[0277] The substrate on which ITO (100 nm), the anode of the organic electroluminescent device, was laminated was patterned by dividing it into cathode and anode regions and an insulating layer through a photolithography process, and then the surface was treated with UV-ozone and O2:N2 plasma for the purpose of increasing the work function of the anode (ITO) and cleaning it.

[0278] Next, 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) was formed as a hole injection layer (HIL) with a thickness of 10 nm on the anode.

[0279] Next, on the hole injection layer, N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) is vacuum-deposited to form a hole transport layer with a thickness of 90 nm, and on the hole transport layer (HTL), N-Phenyl-N-(4-(spiro[benzo[d,e]anthracen-7,9'-fluoren]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine (N-Phenyl-N-(4-(spiro[benzo[d,e]anthracen-7,9'-fluoren]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine) is formed as an electron blocking layer (EBL). [e]anthracene-7,9'-fluorene]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine) was formed with a thickness of 15 nm.

[0280] 9,10-Bis(2-naphthyl)anthracene (ADN) was deposited as a host with a thickness of 25 nm on the electron blocking layer (EBL) 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 was deposited as a dopant. t-DABNA-dtB) was doped at about 3 wt%. As an electron transport auxiliary layer of the light-emitting layer, the compound of the present invention was vacuum-deposited to form a 5 nm thickness as shown in Table 29 below, and 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 were mixed at a weight ratio of 1:1 and deposited to a 25 nm thickness as an electron transport layer (ETL), and 1 nm of Liq was deposited as an electron injection layer on the electron transport layer, and aluminum was deposited to a 100 nm thickness as a cathode. N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited as a capping layer on the above cathode to a thickness of 60 nm.

[0281] Next, a seal cap was bonded to the capping layer (CPL) using a UV-curable adhesive to protect the organic light-emitting device from oxygen (O2) or moisture in the air, thereby manufacturing an organic light-emitting device.

[0282] Examples 2 to 10 and Comparative Examples 1 and 2 manufactured organic light-emitting devices in the same manner as in Example 1, except that the compounds of Table 29 and Comparative Compound 1 and Comparative Compound 2 were used instead of the compound of Example 1 as the electron transport auxiliary layer.

[0283]

[0284] For the organic light-emitting devices of Examples 2 to 10 and Comparative Examples 1 and 2, 10 mA / cm was measured using KONICA MINOLTA CS-2000. 2 The driving voltage (Op V) and efficiency (Cd / A) were measured by applying current, and 10 mA / cm was measured using McScience M6000. 2 The lifespan (LT95) was measured by checking the time it takes for the luminance to decrease from the initial luminance to 95% by constant current driving.

[0285] The measurement results are shown in Table 29 below.

[0286]

[0287] Referring to Table 29, it can be confirmed that the compound of the present invention has high efficiency and long life as a blue OLED device material.

[0288] For the comparative compound, it was confirmed that the efficiency and lifespan of the device were significantly reduced.

[0289] [Experimental Example 4] Electron Transport Layer Device Experiment Results

[0290] The substrate on which ITO (100 nm), the anode of the organic electroluminescent device, was laminated was patterned by dividing it into cathode and anode regions and an insulating layer through a photolithography process, and then the surface was treated with UV-ozone and O2:N2 plasma for the purpose of increasing the work function of the anode (ITO) and cleaning it.

[0291] Next, 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) was formed as a hole injection layer (HIL) with a thickness of 10 nm on the anode.

[0292] Next, on the hole injection layer, N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) is vacuum-deposited to form a hole transport layer with a thickness of 90 nm, and on the hole transport layer (HTL), N-Phenyl-N-(4-(spiro[benzo[d,e]anthracen-7,9'-fluoren]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine (N-Phenyl-N-(4-(spiro[benzo[d,e]anthracen-7,9'-fluoren]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine) is formed as an electron blocking layer (EBL). [e]anthracene-7,9'-fluorene]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine) was formed with a thickness of 15 nm.

[0293] 9,10-Bis(2-naphthyl)anthracene (ADN) was deposited as a host with a thickness of 25 nm on the electron blocking layer (EBL) 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 was deposited as a dopant. t-DABNA-dtB) was doped at about 3 wt%. 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine (2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine) was vacuum-deposited to form a 5 nm thick electron transport layer of the light-emitting layer, and a 25 nm thick compound of Table 30 was deposited as an electron transport layer (ETL) thereon. LiQ was deposited as an electron injection layer with a 1 nm thickness on the electron transport layer, and aluminum was deposited as a 100 nm thick cathode. N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited as a capping layer on the above cathode to a thickness of 60 nm.

[0294] Next, a seal cap was bonded to the capping layer (CPL) using a UV-curable adhesive to protect the organic light-emitting device from oxygen (O2) or moisture in the air, thereby manufacturing an organic light-emitting device.

[0295] Examples 11 to 112 and Comparative Examples 3 and 4 were prepared in the same manner as in Example 30, except that the compounds of Table 30 and Comparative Compound 3 and Comparative Compound 4 were used instead of the compound of Example 11 as the electron transport auxiliary layer.

[0296]

[0297] For the organic light-emitting devices of Examples 11 to 112 and Comparative Examples 3 and 4, 10 mA / cm was measured using KONICA MINOLTA CS-2000. 2 The driving voltage (Op V) and efficiency (Cd / A) were measured by applying current, and 10 mA / cm was measured using McScience M6000. 2 The lifespan (LT95) was measured by checking the time it takes for the luminance to decrease from the initial luminance to 95% by constant current driving.

[0298] The measurement results are shown in Table 30 below.

[0299]

[0300]

[0301]

[0302]

[0303] Referring to Table 30, it can be confirmed that the compound of the present invention has high efficiency and long life as a blue OLED device material.

[0304] For the comparative compound, it was confirmed that the efficiency and lifespan of the device were significantly reduced.

[0305] Although the embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept 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] X is oxygen (O) or sulfur (S), Y1, Y2 and Y3 are nitrogen (N) or CR2, At least two of Y1, Y2 and Y3 are nitrogen (N), Z1, Z2 and Z3 are nitrogen (N) or CR3, L1 and L2 are the same 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, A is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl 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, and can combine with an adjacent group to form a substituted or unsubstituted ring, Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl 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, and can combine with adjacent groups to form a substituted or unsubstituted ring, R1, R2 and R3 are the same or different, 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 arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl 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, and can combine with adjacent groups to form a substituted or unsubstituted ring, p is an integer from 0 to 7, The substituents of L1, L2, A, Ar1, Ar2, R1, R2 and R3 are each independently deuterium, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a trimethylsilyl group (TMS), an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkenyl group having 3 to 20 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a heteroaryl group having 5 to 60 carbon atoms, a heteroarylalkyl group having 6 to 60 carbon atoms, an amine group, an alkylamino group having 1 to 30 carbon atoms, an arylalkylamino group having 7 to 30 carbon atoms, a carbon 6 is substituted with at least one substituent selected from the group consisting of an arylamino 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, and when substituted with multiple substituents, they may be the same as or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring.

2. In paragraph 1, An organic compound, wherein the chemical formula 1 is represented by one of the chemical formulas 2 to 4 below. [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] In the chemical formulas 2 to 4 above, X, L1, L2, A, Ar1, Ar2, R1, and p and their substituents are as defined in the chemical formula 1.

3. First electrode; a second electrode facing the first electrode; and At least one organic layer is included between the first electrode and the second electrode, An organic light-emitting device, wherein at least one of the organic layers comprises an organic compound according to claim 1.

4. In paragraph 3, An organic light-emitting device, wherein the organic layer containing the organic compound according to the first clause is an electron transport auxiliary layer or an electron transport layer.

5. In paragraph 4, An organic light-emitting device, wherein the organic layer further includes at least one selected from a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection layer.

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