Organic compounds and organic light-emitting diode comprising same

Abstract

The purpose of the present invention is to provide novel organic compounds and an organic light-emitting diode comprising same. An organic light-emitting diode comprising the compound represented by chemical formula A-1, B-1 or C-1, according to the present invention, has excellent driving voltage, luminous efficiency, external quantum efficiency (EQE), 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] With the development of display devices, the need for capping layer compounds having high refractive index that can improve the luminous efficiency and lifespan of the devices is increasing.

[0007] Conventionally, the capping layer material is a protective film formed to protect the easily corroded reflective electrode of an organic light-emitting device. Alq3, which has excellent thermal stability, is generally used. However, when deposited, ash is generated to form an uneven thin film, which causes a gap to form between the electrode and the protective film, allowing moisture or oxygen to penetrate, resulting in a short lifespan. Recently, to compensate for this, organic compounds have been used as protective film materials.

[0008] However, in line with the development of display devices that are gradually becoming larger, brighter, and higher resolution for IT / mobile devices, efforts have been made to develop compounds for electrode protective films that have higher refractive index, uniform thin film formation, low deposition temperature, and excellent thermal stability to improve the performance and lifespan of the devices.

[0009] The purpose of the present invention is to provide a novel organic compound and an organic light-emitting device comprising the same.

[0010] In addition to the above-mentioned tasks, embodiments according to the present invention can be used to achieve other tasks not specifically mentioned.

[0011] The present invention is not limited to the purposes mentioned above, and other purposes and advantages of the present invention not mentioned above can be understood through the following description and will be more clearly understood through the embodiments of the present invention. Furthermore, it will be readily apparent that the purposes and advantages of the present invention can be realized by the means and combinations thereof set forth in the claims.

[0012] One embodiment of the present invention can provide a compound represented by the following chemical formula A-1, B-1 or C-1, wherein the definition of the following chemical formula A-1, B-1 or C-1 is the same as that described in the present specification and claims.

[0013] [Chemical Formula A-1]

[0014]

[0015] [Chemical Formula B-1]

[0016]

[0017] [Chemical Formula C-1]

[0018]

[0019] An organic light-emitting device according to one embodiment of the present invention may include a first electrode, a second electrode facing the first electrode, one or more organic layers positioned on the inner side of the first electrode and the second electrode, and a capping layer positioned on the outer side of at least one of the first electrode and the second electrode, and the capping layer may provide an organic light-emitting device including a compound represented by the chemical formula A-1, B-1, or C-1.

[0020] The organic light-emitting device comprising the compound represented by the chemical formula A-1, B-1 or C-1 of the present invention has excellent characteristics such as driving voltage, luminous efficiency, external quantum efficiency (EQE), long life and stability.

[0021] In addition, the compound represented by the chemical formula A-1, B-1 or C-1 of the present invention has a high refractive index (n) of about 2.0 or more and a high transmittance of about 80% or more at a wavelength of 400 nm to 650 nm.

[0022] The above effects and additional effects are described in detail below.

[0023] The above-described purposes, features and advantages are described in detail below, so that a person having ordinary knowledge in the technical field to which the present invention pertains can easily implement the technical idea of ​​the present invention.

[0024] 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.

[0025] 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.

[0026] In interpreting the components in this specification, even if there is no separate explicit description, it is interpreted to include the range of error.

[0027] 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.

[0028] The term “halogen group” as used herein includes fluorine, chlorine, bromine and iodine.

[0029] 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.

[0030] 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.

[0031] 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.

[0032] 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.

[0033] 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.

[0034] 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.

[0035] 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.

[0036] 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, phenanthrel, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, and the like. In addition, an aryl group may be optionally substituted.

[0037] 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 phenoxathienyl, 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] The above substituents are each independently selected from the group consisting of deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, and a arylamino group having 5 to 30 carbon atoms. It may be at least one selected from the group consisting of a heteroarylamino group of 60, 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 there are multiple of them, they are the same or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring.

[0046] Unless specifically limited in this specification, the position to be substituted is not limited as long as it is a position where a hydrogen atom is substituted, i.e., a position where a substituent can be substituted, and when two or more substituents exist, the substituents may be the same or different from each other.

[0047] Each target and substituent defined in this specification may be the same or different unless otherwise specified.

[0048] Hereinafter, the organic compound according to the present invention and the organic light-emitting device including the same will be described in detail.

[0049] According to an embodiment of the present invention, the compound of the present invention can be expressed by the following chemical formula A-1.

[0050] [Chemical Formula A-1]

[0051]

[0052] Here, p and q are integers from 0 to 3,

[0053] L 1, L2 and L3 are the same or different from each other, and are each independently selected from the group consisting of a single 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] Ar1, Ar2, Ar3, Ar4 and Ar5 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, 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.

[0055] R1 and R2 are the same or different, and each independently represent hydrogen, deuterium, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a trimethylsilyl group (TMS), 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkynyl 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 aryl group having 6 to 60 carbon atoms It may be at least one selected from the group consisting of a heteroarylalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, and when substituted with multiple substituents, they may be the same as each other or Different and adjacent groups can combine with each other to form substituted or unsubstituted rings,

[0056] R1 and R2 are the same or different, and each independently represent hydrogen, deuterium, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a trimethylsilyl group (TMS), 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkynyl 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 aryl group having 6 to 60 carbon atoms It may be at least one selected from the group consisting of a heteroarylalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, and when there are multiple ones, they are the same or different from each other. Can combine with adjacent groups to form substituted or unsubstituted rings,

[0057] When p and q are 2 or 3, multiple R1 and R2 may be different substituents,

[0058] The above L1, L2, L3, Ar1, Ar2, Ar3, Ar4, Ar5, The substituents of R1 and R2 are each independently deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, It may be at least one selected from the group consisting of 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, and when there are multiple of them, they are the same or different from each other, and can combine with adjacent groups to form a substituted or unsubstituted ring.

[0059] At least three of the above chemical formulas Ar1 to Ar6 may be compounds having the following structure:

[0060]

[0061] X a1 and X a2 may be the same or different, and each independently represents oxygen (O), sulfur (S), N (R) a1 ) is selected from the group consisting of,

[0062] R a1is 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,

[0063] The above R a1 The substituents of each independently are deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, a arylamino group having 5 to It may be at least one selected from the group consisting of a heteroarylamino group of 60, 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 there are multiple of them, they are the same or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring.

[0064] The above chemical formulas Ar1 to Ar6 may have three compounds of the above structures.

[0065] According to an embodiment of the present invention, the compound of the above chemical formula A-1 can be expressed by the following chemical formula A-2.

[0066] [Chemical Formula A-2]

[0067]

[0068] Here, X1, X2, X 3, X4, X5 and X6 may be the same or different, and each independently represents oxygen (O), sulfur (S), N (R) 10 ) and C(R 11 )(R 12 ) is selected from the group consisting of,

[0069] R3, R4, R5, R6, R7, R8R9, R 10 , R 11 and R 12 may be the same 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 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 may combine with adjacent groups to form a substituted or unsubstituted ring,

[0070] The above R3, R4, R5, R6, R7, R8R9, R 10 , R 11 and R 12The substituents of each independently are deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, a arylamino group having 5 to It may be at least one selected from the group consisting of a heteroarylamino group of 60, 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 there are multiple of them, they are the same or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring,

[0071] L1 and L3 are as defined in the above chemical formula A-1.

[0072] According to an embodiment of the present invention, the compound of the above chemical formula A-1 can be expressed by the following chemical formula A-3.

[0073] [Chemical Formula A-3]

[0074]

[0075] Here, X1, X2, X 3, X4, X 5, X 6, R3, R 4, R5, R 6, R7, R8 and R9 are as defined in the above chemical formula A-2.

[0076] According to an embodiment of the present invention, the compound of the above chemical formula A-1 can be expressed by the following chemical formula A-4.

[0077] [Chemical Formula A-4]

[0078]

[0079] Here, L2, L3, X1, X2, X 3, X4, X 5, X 6, R 3, R 4, R 5, R 7, R8 and R9 are as defined in the above chemical formulas A-1 and A-2,

[0080] R 13 may be the same 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 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 may combine with adjacent groups to form a substituted or unsubstituted ring,

[0081] The above R 13The substituents of each independently are deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, a arylamino group having 5 to It may be at least one selected from the group consisting of a heteroarylamino group of 60, 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 there are multiple of them, they are the same or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring,

[0082] r is an integer from 0 to 5,

[0083] If r is 2, 3, 4, or 5, multiple R 13 may be different substituents.

[0084] According to an embodiment of the present invention, the compound of the above chemical formula A-1 can be expressed by the following chemical formula A-5.

[0085] [Chemical Formula A-5]

[0086]

[0087] Here, X1, X2, X 3, X4, X 5, X 6, R 3, R 4, R 5,R 7, R8 and R9 are as defined in the above chemical formula A-2,

[0088] R 13 and r are as defined in the above chemical formula A-4.

[0089] According to an embodiment of the present invention, the compound of the above chemical formula A-1 can be expressed by the following chemical formula A-6.

[0090] [Chemical Formula A-6]

[0091]

[0092] Here, L2, L 3, X1, X2, X 3, X4, X 5, X 6, R3, R 4, R5, R7, R8 and R9 are as defined in the above chemical formulas A-1 and A-2.

[0093] According to an embodiment of the present invention, the compound of the above chemical formula A-1 can be expressed by the following chemical formula A-7.

[0094] [Chemical Formula A-7]

[0095]

[0096] Here, L2, L 3, X1, X2, X 3, X4, X 5, X 6, R3, R 4, R5, R7, R8 and R9 are as defined in the above chemical formulas A-1 and A-2.

[0097] According to an embodiment of the present invention, the compound of the present invention can be expressed by the following chemical formula B-1.

[0098] [Chemical Formula B-1]

[0099]

[0100] X b1 , X b2 , X b3, X b4 and Xb5 may be the same or different, and each independently represents oxygen (O), sulfur (S), and N (R) b7 ) is selected from the group consisting of,

[0101] L b1 and L b2 are identical 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,

[0102] Ar b1 is selected from the group consisting of hydrogen, 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,

[0103] R b1 , R b2 , R b3 , R b4 , R b5 , R b6 and R b7are the same 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 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,

[0104] L b1 , L b2 , Ar b1 , R b1 , R b2 , R b3 , R b4 , R b5 , R b6 and R b7The substituents of each independently are deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, a arylamino group having 5 to It may be at least one selected from the group consisting of a heteroarylamino group of 60, 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 there are multiple of them, they are the same or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring.

[0105] According to an embodiment of the present invention, the L b1 It can be a direct bond or a divalent phenylene group.

[0106] According to an embodiment of the present invention, the L b2 may be a trivalent phenylene group.

[0107] According to an embodiment of the present invention, the organic compound of the chemical formula B-1 can be expressed by the following chemical formulas B-2 and B-3.

[0108] L in the following chemical formulas B-2 and B-3 b1 , L b2 , Ar b1 , R b1 , R b2 , R b3 , R b4 , Rb5 , R b6 and R b7 And its substituents are as defined in the above chemical formula B-1.

[0109] [Chemical Formula B-2]

[0110]

[0111] [Chemical Formula B-3]

[0112]

[0113] The chemical formula Ar b1 may be a compound of the following structure,

[0114]

[0115] X b6 and X b7 may be the same or different, and each independently represents oxygen (O), sulfur (S), and N (R) b8 ) is selected from the group consisting of,

[0116] R b8 is 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,

[0117] The above R b8The substituents of each independently are deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, a arylamino group having 5 to It may be at least one selected from the group consisting of a heteroarylamino group of 60, 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 there are multiple of them, they are the same or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring.

[0118] According to an embodiment of the present invention, the compound of the present invention can be represented by the following chemical formula C-1.

[0119] [Chemical Formula C-1]

[0120]

[0121] Here, cp and cq are integers from 0 to 3,

[0122] Y c1 may be the same or different, and each independently represents oxygen (O), sulfur (S), N (R) c3 ) is selected from the group consisting of,

[0123] L c1 and L c2are identical 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,

[0124] Ar c1 Inland Ar c4 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, 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,

[0125] Ar c1 Inland Ar c4 and R c3 At least three of them are compounds having the following structure,

[0126]

[0127] Here, cr1 is an integer from 0 to 4,

[0128] Here, Y c2 and Y c3 may be the same or different, and each independently represents oxygen (O), sulfur (S), N (R) c4 ) is selected from the group consisting of,

[0129] Ar c1 Inland Arc4 and R c3 At least one of them contains CN (Cyano group),

[0130] R c1 , R c2 , R c3 and R c4 is selected from the group consisting of hydrogen, a small number of 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 adjacent groups to form a substituted or unsubstituted ring,

[0131] L c1 , L c2 , Ar c1 , Ar c2 , Ar c3 , Ar c4 , R c1 , R c2 , R c3 and R c4The substituents of each independently are deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, a arylamino group having 5 to It may be at least one selected from the group consisting of a heteroarylamino group of 60, 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 there are multiple of them, they are the same or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring.

[0132] According to an embodiment of the present invention, the organic compound of the chemical formula C-1 can be expressed by the following chemical formulas C-2 to C-9.

[0133] Yc1, L in the following chemical formulas C-2 to C-9 c1 and L c2 and its substituents are as defined in the above chemical formula C-1,

[0134] cr2 to cr4 are integers from 0 to 4,

[0135] cr5 is an integer from 0 to 5,

[0136] Yc4 to Yc9 may be the same or different, and each independently represents oxygen (O), sulfur (S), N (R) c12) is selected from the group consisting of,

[0137] L c3 is 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,

[0138] R c5 Inland R c13 are the same 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 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,

[0139] L c3 and R c5 Inland R c13The substituents of each independently are deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, a arylamino group having 5 to It may be at least one selected from the group consisting of a heteroarylamino group of 60, 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 there are multiple of them, they are the same or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring.

[0140] [Chemical Formula C-2]

[0141]

[0142] [Chemical Formula C-3]

[0143]

[0144] [Chemical Formula C-4]

[0145]

[0146] [Chemical Formula C-5]

[0147]

[0148] [Chemical Formula C-6]

[0149]

[0150] [Chemical Formula C-7]

[0151]

[0152] [Chemical Formula C-8]

[0153]

[0154] [Chemical Formula C-9]

[0155]

[0156] According to an embodiment of the present invention, the direct bond or single bond is L1, L2, L3, L in the chemical formula b1 , L b2 , L c1 , L c2 or L c3 As in the absence of L1, L2, L3, L b1 , L b2 , L c1 , L c2 or L c3 It means that the components of the chemical formula on both sides are directly combined.

[0157] According to an embodiment of the present invention, the arylene group may be a divalent phenylene group having the following structure, and the divalent phenylene group means a phenylene group having six positions capable of substitution bonding in which two positions are substituted. This may be any one of 1,2 (ortho) substitution, 1,3 (meta) substitution, and 1,4 (para) substitution, and may be selected from the following structures.

[0158]

[0159] According to an embodiment of the present invention, the arylene group may be a trivalent phenylene group having the following structure, and the trivalent phenylene group means that three positions are substituted in a six-position phenylene group capable of substitution bonding. This may be any one of 1,2,3 substitution, 1,2,4 substitution, 1,2,5 substitution, 1,2,6 substitution, 1,3,4 substitution, 1,3,5 substitution, 1,3,6 substitution, 1,4,5 substitution, and 1,4,6 substitution, and may be selected from the following structures.

[0160]

[0161] According to an embodiment of the present invention, in the compound of the present invention, L1, L2, L3, Ar1, Ar2, Ar3, Ar4, Ar 5, X1, X2, X 3, X4, X5, X6, X a1 , R1, R2, R3, R 4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 and R a1 and L b1 , L b2 , Ar b1 , X b1 , X b2 , X b3 , X b4 , X b5 , X b6 , X b7 R b1 , R b2 , R b3 , R b4 , R b5 , R b6 , R b7 and R b8 and L c1 , L c2 , L c3 , Ar c1 , Ar c2 , Ar c3 , Ar c4 , Y c1 , Y c2 , Y c3 , Y c4 , Y c5 , Y c6 , Y c7 , Y c8 , Y c9 , R c1 , R c2 , R c3 R c4 , R c5 , R c6 , R c7 , R c8, R c9, R c10 , R c11 , R c12 and R c13 Depending on the type and bonding position, the direction and size of the dipole moment of the compound molecules can be controlled. Through this, the electrostatic attraction between molecules can be controlled, and as a result, the packing density of the thin film formed from the compound and the crystallinity of the compound can be controlled. If the packing density of the thin film increases, the refractive index can be increased, but due to the high crystallinity, a clogging phenomenon can occur in which crystalline materials accumulate in the raw material inlet and passage during the organic light-emitting device manufacturing process, which can reduce the productivity of the device and the uniformity of the thin film.

[0162] According to an embodiment of the present invention, in the compound of the present invention, L1, L2, L3, Ar1, Ar2, Ar3, Ar4, Ar 5, X1, X2, X 3, X4, X5, X6, X a1 , R1, R2, R3, R 4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 and R a1 and L b1 , L b2 , Ar b1 , X b1 , X b2 , X b3 , X b4 , X b5 , X b6 , X b7 R b1 , R b2 , R b3 , R b4 , R b5 , R b6 , R b7 and R b8 and L c1 , L c2 , L c3 , Arc1 , Ar c2 , Ar c3 , Ar c4 , Y c1 , Y c2 , Y c3 , Y c4 , Y c5 , Y c6 , Y c7 , Y c8 , Y c9 , R c1 , R c2 , R c3 R c4 , R c5 , R c6 , R c7 , R c8, R c9 , R c10 , R c11 , R c12 and R c13 By selecting the type and bonding position, a compound is disclosed that maintains a high refractive index while causing less blockage.

[0163] According to an embodiment of the present invention, in the compound of the present invention, the types and positions of the binding functional groups on the left and right sides are selected differently, with the nitrogen (N) of the carbazole core or the oxygen (O) (or sulfur (S)) of the dibenzofuran (or dibenzothiophene) core as the center, so that this can be implemented through an asymmetric compound structure.

[0164] In addition, according to an embodiment of the present invention, in the case of a compound introducing a cyano group (-CN group), polarization is easily achieved throughout the molecular structure due to the strong electron withdrawing effect of the cyano group. As a result, dipole-dipole interaction between molecules increases, thereby increasing packing density. Therefore, the density of a compound introducing a cyano group (-CN group) increases compared to other compounds, thereby increasing the refractive index.

[0165] According to one embodiment of the present invention, the compounds represented by chemical formulas A-1 to A-7 may be composed of fragment A and partial fragment D, but are not limited thereto. (In the partial compounds below, * indicates a portion where the partial compounds are bonded by a single bond.)

[0166] The above fragment A may have the following structure, but is not limited thereto.

[0167]

[0168] According to one embodiment of the present invention, the compounds represented by chemical formulas B-1 to B-3 may be composed of fragment B and fragment D, but are not limited thereto. (In the following partial compounds, * indicates a portion where the partial compounds are bonded by a single bond.)

[0169] The above fragment B may have the following structure, but is not limited thereto.

[0170]

[0171]

[0172] According to one embodiment of the present invention, the compounds represented by chemical formulas C-1 to C-9 may be composed of fragment C and fragment D, but are not limited thereto. (In the following partial compounds, * indicates a portion in which the partial compounds are bonded by a single bond.)

[0173] The above fragment C may have the following structure, but is not limited thereto.

[0174]

[0175] The above segment (fragment D) may have the following structure, but is not limited thereto.

[0176]

[0177] According to one embodiment of the present invention, the compound represented by chemical formula A-1, B-1 or C-1 may be selected from the group consisting of the following compounds, but is not limited thereto.

[0178]

[0179] The organic light-emitting device of the present invention may include a first electrode, a second electrode facing the first electrode, one or more organic layers positioned on the inner side of the first electrode and the second electrode, and a capping layer positioned on the outer side of at least one of the first electrode and the second electrode, and the capping layer may provide an organic light-emitting device including at least one selected from compounds represented by the chemical formula A-1, B-1, or C-1.

[0180] In the organic light-emitting device according to an embodiment of the present invention, the transmittance of the compound of the present invention in the wavelength band of 400 to 650 nm may be greater than about 80% (absorption rate constant (K) value is 0.02). For example, the transmittance of the compound represented by the chemical formula A-1, B-1, or C-1 in the wavelength band of 400 to 650 nm may be 82% or more, 84% or more, 86% or more, 88% or more, 89% or more, 90% or more, 91% or more, 92% or more, 93% or more, 94% or more, 95% or more, or 96% or more.

[0181] According to an embodiment of the present invention, the compound represented by the chemical formula A-1, B-1 or C-1 can absorb high-energy wavelengths of less than about 400 nm, and thus, a capping layer including the compound represented by the chemical formula A-1, B-1 or C-1 can minimize damage to organic materials inside the device. In addition, since the compound transmits most wavelengths of 400 to 650 nm or more, the luminous efficiency and external quantum efficiency of the organic light-emitting device can be improved.

[0182] According to an embodiment of the present invention, the refractive index of the compound of the present invention may be 2.0 or more. For example, the refractive index of the compound represented by the chemical formula A-1, B-1, or C-1 in the wavelength band of 400 to 650 nm may be 2.05 or more, 2.10 or more, 2.15 or more, 2.20 or more, or 2.25 or more. Accordingly, the organic light-emitting device including the compound represented by the chemical formula A-1, B-1, or C-1 can reduce light loss due to total reflection.

[0183] However, the upper limit of the refractive index of the compound of the present invention is not separately determined, but for optimization, it may be 2.5 or less, 2.75 or less, or 3.0 or less.

[0184] The organic material layer of the organic light-emitting device according to an embodiment of the present invention 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, and may additionally include a charge generation layer, a hole transport auxiliary layer, a light-emitting auxiliary layer, an electron transport auxiliary layer, etc.

[0185] 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.

[0186] 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).

[0187] 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).

[0188] 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.

[0189] The above-described luminescent compound of the 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.

[0190] 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 may 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-hydroxyquinolinolato)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.

[0191] Above, 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).

[0192] The above electron injection layer or electron transport layer compound is not particularly limited, and any compound that is typically used as an electron injection layer or electron transport 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-hydroxyquinolinolato)aluminum (Alq3), LiF, Liq, Li2O, BaO, NaCl, and CsF.

[0193] The above second electrode (cathode) 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, a transparent cathode through which light can pass may be formed using indium tin oxide (ITO) or indium zinc oxide (IZO).

[0194] Above, a capping layer according to an embodiment may be positioned on the surface of the second electrode. The capping layer may include one or more compounds selected from the compounds represented by the above chemical formula A-1, B-1, or C-1.

[0195] The capping layer may include an additional capping layer compound.

[0196] As mentioned above, the capping layer compound is not particularly limited, and any compound that is commonly used as a capping layer compound can be used. Non-limiting examples of capping layer compounds include arylamine derivatives such as N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, carbazole derivatives, pyridine derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, quinoline derivatives, isoquinoline derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), tris(8- It may contain substances such as hydroxyquinolinato (hydroxyquinolinolato) aluminum (Alq3), LiF, Liq, Li2O, BaO, NaCl, CsF, etc.

[0197] An organic light-emitting device according to one embodiment of the present invention may include a plurality of capping layers, and at least one of the plurality of capping layers or all of the plurality of capping layers may include one or more compounds selected from the compounds represented by A-1, B-1, or C-1.

[0198] The organic light-emitting device according to an embodiment of the present invention may be a front-emitting device or a back-emitting device.

[0199] The thickness of the capping layer of the organic light-emitting device according to an embodiment of the present invention may be about 300 to 1500 Å, or about 500 to 1200 Å, or about 600 to 1000 Å.

[0200] In the organic light-emitting device according to the embodiment of the present invention, the density of the capping layer is about 1.15 to 1.35 g / cm 3 may be, or about 1.2 to 1.3 g / cm 3 Within this density range, the efficiency of the device can be further improved.

[0201] An organic light-emitting device according to an embodiment of the present invention can be used in a display device.

[0202] The organic light-emitting device according to an embodiment of the present invention can be applied to transparent display devices, mobile display devices, flexible display devices, etc., but is not limited thereto. The capping layer according to the embodiment exhibits high transmittance suitable for transparent display devices and has high tensile strength suitable for flexible display devices.

[0203] Synthetic example

[0204] 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.

[0205] L1, L2, L3, Ar1, Ar2, Ar3, Ar4, Ar described in the general reaction formulas Scheme A-1, A-2, B, C-1, C-2, C-3 below 5, X1, X2, X 3, X4, X5, X6, X a1 , R1, R2, R3, R 4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 and R a1 and L b1 , L b2 , Ar b1 , X b1 , X b2 , X b3 , X b4 , X b5 , X b6 , X b7 R b1 , R b2 , R b3 , R b4 , R b5 , R b6 , R b7 and R b8 and L c1 , L c2 , L c3 , Ar c1 , Ar c2 , Ar c3 , Ar c4 , Y c1 , Y c2 , Y c3 , Y c4 , Y c5 , Y c6 , Y c7 , Y c8 , Y c9 , R c1 , R c2 , R c3 R c4 , R c5 , R c6 , R c7 , R c8, R c9 , R c10 , R c11, R c12 and R c13 is as defined in the above chemical formulas A-1 to A-7, B-1 to B-3 and C-1 to C-9.

[0206] In the following reaction formula, Halogen refers to a halogen group, but any equivalent substituent of the halogen leaving group is possible.

[0207] In the following reaction formula, Boronic compound refers to boronic acid, boronic ester, dioxaborolane, etc., but all equivalent substituents of the boronic leaving group are possible.

[0208] In the following reaction formula, the solvent, catalyst, etc. are representative examples, and all equivalent solvents, catalysts, etc. are possible.

[0209] [Response Plan A]

[0210] Compound A can be synthesized as follows, but is not limited thereto.

[0211] [General reaction formula Scheme A-1]

[0212]

[0213] [General reaction formula Scheme A-2]

[0214]

[0215] [Representative reaction formula A-1]

[0216]

[0217] In a 200 mL flask under a nitrogen flow, reactant A (20 mmol, 9.6 g), reactant 1 (20 mmol, 5.5 g), NaOtBu (60 mmol, 5.9 g), Pd2(dba)3 (1.0 mmol, 0.9 g), X-phos (2.0 mmol, 0.95 g), and 1,4-dioxane (200 mL) were added 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 Product A-1.

[0218] [Representative Reaction Scheme A-10]

[0219]

[0220] In a 500 mL flask under a nitrogen atmosphere, reactant A' (20 mmol, 10.0 g), reactant 2 (20 mmol, 7.8 g), K2CO3 (60 mmol, 8.3 g), Pd(PPh3)4 (0.1 mmol, 1.2 g), 1,4-Dioxane (200 mL), and water (40 mL) were added 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 A-10.

[0221] Compound A was synthesized using the same or similar method as above.

[0222] [Response Plan B]

[0223] Compound A can be synthesized as follows, but is not limited thereto.

[0224] [General reaction formula Scheme B]

[0225]

[0226] [Representative reaction formula B-1]

[0227]

[0228] In a 500 mL flask under a nitrogen atmosphere, reactant B (20 mmol, 10.0 g), reactant 3 (20 mmol, 7.8 g), K2CO3 (60 mmol, 8.3 g), Pd(PPh3)4 (0.1 mmol, 1.2 g), 1,4-Dioxane (200 mL), and H2O (40 mL) were added 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 Product B-1.

[0229] Compound B was synthesized using the same or similar method as above.

[0230] [Response Plan C]

[0231] Compound C can be synthesized as follows, but is not limited thereto.

[0232] [General reaction formula Scheme C-1]

[0233]

[0234] [General reaction formula Scheme C-2]

[0235]

[0236] [General reaction formula Scheme C-3]

[0237]

[0238] [Representative reaction scheme C-1]

[0239]

[0240] In a 500 mL flask under a nitrogen atmosphere, reactant S (20 mmol, 9.6 g), reactant 4 (20 mmol, 5.5 g), NaOtBu (60 mmol, 5.9 g), Pd2(dba)3 (1.0 mmol, 0.9 g), X-phos (2.0 mmol, 0.95 g), and 1,4-dioxane (200 mL) were added 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 Product C-1.

[0241] [Representative reaction formula C-16]

[0242]

[0243] In a 500 mL flask under a nitrogen atmosphere, Reactant C' (20 mmol, 10.0 g), Reactant 5 (20 mmol, 7.8 g), K2CO3 (60 mmol, 8.3 g), Pd(PPh3)4 (0.1 mmol, 1.2 g), 1,4-Dioxane (200 mL), and water (40 mL) were added 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 Product C-16.

[0244] [Representative Reaction Formula C-233]

[0245]

[0246] In a 500 mL flask under a nitrogen atmosphere, Reactant C'' (20 mmol, 10.0 g), Reactant 6 (20 mmol, 7.8 g), K2CO3 (60 mmol, 8.3 g), Pd(PPh3)4 (0.1 mmol, 1.2 g), 1,4-Dioxane (200 mL), and water (40 mL) were added 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 and recrystallized to obtain Product C-233.

[0247] Compound C was synthesized using the same or similar method as above.

[0248] Representative synthesized compounds are shown in Tables 1 to 6 below, and the specific compounds of the present invention and similar compounds can be synthesized through the above synthetic examples.

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255] Experimental Example 1 - Confirmation of single-film characteristics (refractive index and transmittance)

[0256] To measure the optical properties (refractive index and transmittance) of the compound, a vacuum of 9×10 was placed on a glass substrate (0.7T). -7 A single film was produced by depositing 1,000Å of the compounds in Table 2 below on a glass substrate at a rate of 1Å / sec at Torr.

[0257] As shown in Table 2 below, the n (refractive index) and k (extinction coefficient) of the single film for optical property evaluation were measured using an Ellipsometer from JA WOOLLAM for each single film forming material compound.

[0258] As a comparative example, a single film was manufactured in the same manner as in Experimental Example 1, except that Comparative Compound 1 and Comparative Compound 2 were used, and the refractive index and transmittance were measured.

[0259] [Comparative Compound 1]

[0260]

[0261] [Comparative Compound 2]

[0262]

[0263] Single-film forming material 460 nm 520 nm 620 nm Refractive index Transmittance Refractive index Transmittance Refractive index Transmittance Compound A-12.2895.22.1791.42.0989.7 Compound A-22.2496.02.1592.12.0889.8 Compound A-32.2996.02.1991.92.1089.5 Compound B-12.3194.32.2190.62.1189.1 Compound B-22.2995.82.2291.52.1089.4 Compound B-32.3095.42.1991.72.1189.6 Compound B-42.3196.22.2092.02.1689.9Comparative compound 11.9898.01.8591.01.8488.0Comparative compound 21.7864.01.7368.01.6964.0

[0264] As shown in Table 7 above, when analyzing the optical properties, it can be confirmed that the single films formed with each compound of the present invention all have a high refractive index of 2.0 or higher.

[0265] When examining the transmittance at wavelengths of 460 nm, 520 nm, and 620 nm of the single films formed with each compound of the present invention, it can be confirmed that they all have high transmittances of 80% or more.

[0266] As shown in Table 2 above, it was confirmed that the compound used as a conventional capping layer material had a superior refractive index and high transmittance compared to the comparative compounds 1 and 2.

[0267] Experimental Example 2 - Confirmation of Device Characteristics

[0268] In order to confirm the device characteristics of the compound, examples and comparative examples were prepared as follows.

[0269] [Manufacture of Example 1]

[0270] 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.

[0271] 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.

[0272] 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.

[0273] 9,10-Bis(2-naphthyl)anthracene (AND) 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%. On top of that, 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 thickness of 25 nm as an electron transport layer (ETL). An electron injection layer (LiQ) was deposited to a thickness of 1 nm on the electron transport layer, and aluminum was deposited to a thickness of 100 nm as a cathode.

[0274] Compound A-1 of Table 3 below was deposited as a capping layer on the above cathode to a thickness of 1,000 Å.

[0275] Next, a seal cap was bonded with a UV-curable adhesive on the capping layer (CPL) to protect the organic light-emitting device from oxygen (O2) or moisture in the air, thereby manufacturing an organic light-emitting device Example 1.

[0276] Examples 2 to 34 produced organic light-emitting devices in the same manner as in Example 1, except that the compounds in Table 3 were used instead of A-1 in Example 1 as the capping layer.

[0277] As a comparative example, an organic light-emitting device was manufactured in the same manner as in Example 1 except that comparative compounds 3 to 5 were used.

[0278] [Comparative Compound 3]

[0279]

[0280] [Comparative Compound 4]

[0281]

[0282] [Comparative Compound 5]

[0283]

[0284] For the organic light-emitting devices of Examples 1 to 34 and Comparative Examples 3 to 5, 10 mA / cm was applied using KONICA MINOLTA CS-2000. 2 The efficiency (Cd / A) was measured by applying current, and 10mA / 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 8 below.

[0286] Examples / Comparative Examples Capping Layer Material Efficiency (Cd / A) Lifetime (LT95) Example 1 Compound A-16.5198 Example 2 Compound A-26.6198 Example 3 Compound A-36.5202 Example 4 Compound C-16.8197 Example 5 Compound C-27.1198 Example 6 Compound C-37.0201 Example 7 Compound C-47.0198 Example 8 Compound A-107.5201 Example 9 Compound A-127.6203 Example 10 Compound A-117.7204 Example 11 Compound A-757.5200 Example 12 Compound A-1607.6202 Example 13 Compound A-2017.5200 Example 14 Compound A-1177.6201 Example 15 Compound C-158.3203 Example 16 Compound C-168.4202 Example 17 Compound C-178.3203 Example 18 Compound C-188.4199 Example 19 Compound C-118.3208 Example 20 Compound C-128.5204 Example 21 Compound C-138.6202 Example 22 Compound C-148.5202 Example 23 Compound B-17.2204 Example 24 Compound B-27.3205 Example 25 Compound B-36.9201 Example 26 Compound B-47.1202 Example 27 Compound C-2337.6200 Example 28 Compound C-2347.7202 Example 29 Compound C-2357.9198 Example 30 Compound C-2368.0197 Example 31 Compound B-427.1204 Example 32 Compound B-447.2196 Example 33 Compound C-1277.6201 Example 34 Compound C-1287.7204 Comparative Example 3 Comparative Compound 34.6164 Comparative Example 4 Comparative Compound 44.4166 Comparative Example 5 Comparative Compound 54.5165

[0287] As seen in Table 8, it can be confirmed that the compound of the present invention has excellent efficiency and lifespan in the device.

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

[0289] 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 A-1: [Chemical Formula A-1] Here, p and q are integers from 0 to 3, L 1, L2 and L3 are the same or different from each other, and are each independently selected from the group consisting of a single 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, Ar2, Ar3, Ar4 and Ar5 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, 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 and R2 are the same or different, and each independently represent hydrogen, deuterium, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a trimethylsilyl group (TMS), 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkynyl 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 aryl group having 6 to 60 carbon atoms It may be at least one selected from the group consisting of a heteroarylalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 5 to 60 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, and when there are multiple ones, they are the same or different from each other. Can combine with adjacent groups to form substituted or unsubstituted rings, When p and q are 2 or 3, multiple R1 and R2 may be different substituents, The above L1, L2, L3, Ar1, Ar2, Ar3, Ar4, Ar5, The substituents of R1 and R2 are each independently deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, It may be at least one selected from the group consisting of 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, and when there are multiple of them, they are the same or different from each other, and can combine with adjacent groups to form a substituted or unsubstituted ring.

2. An organic compound represented by the following chemical formula B-1: [Chemical Formula B-1] X b1 , X b2 , X b3 , X b4 and X b5 may be the same or different, and each independently represents oxygen (O), sulfur (S), and N (R) b7 ) is selected from the group consisting of, L b1 and L b2 are identical 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, Ar b1 is selected from the group consisting of hydrogen, 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, R b1 , R b2 , R b3 , R b4 , R b5 , R b6 and R b7 are the same 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 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, Above L b1 , L b2 , Ar b1 , R b1 , R b2 , R b3 , R b4 , R b5 , R b6 and R b7 The substituents of each independently are deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, a arylamino group having 5 to It may be at least one selected from the group consisting of a heteroarylamino group of 60, 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 there are multiple of them, they are the same or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring.

3. An organic compound represented by the following chemical formula C-1: [Chemical Formula C-1] Here, cp and cq are integers from 0 to 3, Y c1 may be the same or different, and each independently represents oxygen (O), sulfur (S), N (R) c3 ) is selected from the group consisting of, L c1 and L c2 are identical 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, Ar c1 Inland Ar c4 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, 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, Ar c1 Inland Ar c4 and R c3 At least three of them are compounds having the following structure, Here, cr1 is an integer from 0 to 4, Here, Y c2 and Y c3 may be the same or different, and each independently represents oxygen (O), sulfur (S), N (R) c4 ) is selected from the group consisting of, Ar c1 Inland Ar c4 and R c3 At least one of them contains CN (Cyano group), R c1 , R c2 , R c3 and R c4 is selected from the group consisting of hydrogen, a small number of 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 adjacent groups to form a substituted or unsubstituted ring, L c1 , L c2 , Ar c1 , Ar c2 , Ar c3 , Ar c4 , R c1 , R c2 , R c3 and R c4 The substituents of each independently are deuterium, a cyano group, 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, an arylamino group having 6 to 30 carbon atoms, a arylamino group having 5 to It may be at least one selected from the group consisting of a heteroarylamino group of 60, 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 there are multiple of them, they are the same or different from each other, and may combine with adjacent groups to form a substituted or unsubstituted ring.

4. First electrode, A second electrode opposite to the first electrode, One or more organic layers located on the inner side of the first electrode and the second electrode, and A capping layer positioned on the outer side of at least one of the first electrode and the second electrode, An organic light-emitting device, wherein the capping layer comprises any one of the compounds of claims 1 to 3.

5. In paragraphs 1 to 3, An organic compound characterized in that the compound having the chemical formulas A-1, B-1 and C-1 has a refractive index of 2.0 or more in the wavelength band of 400 to 650 nm.

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