Organic compounds and organic light-emitting devices comprising the same

Abstract

The present application is to provide a novel organic compound and an organic light emitting device comprising the same. The organic light emitting device comprising the compound represented by Chemical Formula 1 of the present application has excellent characteristics such as driving voltage, luminous efficiency, external quantum efficiency (EQE), long lifespan, and stability.

Description

Technical Field

[0001] This invention relates to an organic compound and an organic light-emitting device containing the same. Background Technology

[0002] Compared with other flat panel display devices such as liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), organic light-emitting devices (OLEDs) have many advantages in terms of simple structure and manufacturing process. They also have high brightness and excellent viewing angle characteristics, as well as fast response speed and low driving voltage. Therefore, they are being actively developed and commercialized as light sources for flat panel displays such as wall-mounted TVs (TVs) or for backlighting, illumination, and advertising boards.

[0003] Organic light-emitting devices consist of an organic layer between two electrodes. They are devices that utilize the principle that electrons and holes are injected into the light-emitting layer from the two electrodes respectively. When electrons and holes combine, they generate excitons. When the generated excitons descend from the excited state to the ground state, they emit light.

[0004] Organic light-emitting devices (OLEDs) may include at least one light-emitting layer. Typically, OLEDs with multiple light-emitting layers include light-emitting layers that emit light with different peak wavelengths, and a specific color is achieved by combining light with different peak wavelengths.

[0005] Such organic light-emitting devices can be divided into top-emitting devices and bottom-emitting devices. Top-emitting devices use a reflective cathode to emit light emitted from the light-emitting layer towards the translucent anode side. Conversely, bottom-emitting devices use a reflective anode to emit light emitted from the light-emitting layer and reflected by the anode towards the transparent cathode side, which is the direction in which the thin-film transistor is driven.

[0006] On the other hand, the biggest problems in organic light-emitting devices (OLEDs) are lifespan and efficiency. As displays become increasingly larger, these efficiency and lifespan issues must be addressed. In OLEDs, the characteristics of the components contained in each layer of the organic film, which consists of one or more layers including the light-emitting layer, located between the anode and cathode, affect the device's driving voltage, luminous efficiency, and brightness. Therefore, these characteristics affect the device's lifespan.

[0007] Therefore, research is actively underway on the components contained in each layer of the organic film. Summary of the Invention

[0008] Technical issues

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

[0010] In addition to the technical problems mentioned above, embodiments of the present invention can also be used to solve other technical problems not specifically mentioned.

[0011] The present invention is not limited to the above-described objectives. Other objectives and advantages of the invention not mentioned in the following description will be understood, and will be more clearly understood through the embodiments of the invention.

[0012] Furthermore, it is understood that the objectives and advantages of the present invention can be achieved by the means and combinations thereof shown in the claims.

[0013] Technical solution

[0014] To solve the aforementioned technical problem, according to an embodiment of the present invention, an organic compound with a novel structure represented by the following chemical formula 1 can be provided, wherein the definition of the following chemical formula 1 is the same as that described in this specification and the scope of protection of the invention.

[0015] Chemical Formula 1:

[0016]

[0017] According to another embodiment of the present invention, an organic light-emitting device comprising an organic compound represented by chemical formula 1 of the present invention can be provided, which may include: a first electrode; a second electrode disposed opposite to the first electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer may include an electron transport layer and / or an electron transport auxiliary layer.

[0018] The effects of the invention

[0019] The organic compound represented by chemical formula 1 of the present invention can achieve excellent electron transport properties.

[0020] Furthermore, one or more of the electron transport layer and electron transport auxiliary layer of the organic light-emitting device of the present invention contain the organic compound represented by chemical formula 1 of the present invention, thereby improving the driving voltage, efficiency and lifetime characteristics of the organic light-emitting device.

[0021] Furthermore, the organic light-emitting device of the present invention contains the organic compound represented by chemical formula 1 of the present invention in the electron transport layer and / or electron transport auxiliary layer, which can excellently achieve the color coordinates targeted by the light-emitting layer even when combined with a light-emitting layer of any color.

[0022] The effects of this specification are not limited to those described above. Those skilled in the art will clearly understand other effects not mentioned from the following description.

[0023] The above effects and additional effects will be described in detail below. Detailed Implementation

[0024] The foregoing objectives, features, and advantages will be described in detail below, and those skilled in the art to which this invention pertains can easily implement the technical ideas of this invention.

[0025] In the course of this specification, detailed descriptions of relevant prior art will be omitted when it is determined that such detailed descriptions may unnecessarily obscure the essence of this specification.

[0026] In this specification, when words such as "including," "having," "forming," "setting," and "possessing" are used to describe structural elements, other parts may be added unless "only" is used. When a structural element is expressed in the singular, it includes cases expressed in the plural, unless otherwise expressly stated.

[0027] In the explanation of structural elements in this specification, even if not explicitly stated separately, they are to be interpreted as including the range of error.

[0028] In this specification, when any structure is provided on the "upper (or lower) part" or "upper (or lower) part" of a structural element, it can indicate not only that the arbitrary structure is in contact with the upper (or lower) part of the structural element, but also that there is another structure between the structural element and any structure provided on (or below) the structural element.

[0029] The term "halogen group" as used in this specification includes fluorine, chlorine, bromine, and iodine.

[0030] As used in this specification, the term "alkyl" refers to both straight-chain alkyl radicals and branched-chain alkyl radicals. Unless otherwise specified, 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, isopentyl, hexyl, etc. Furthermore, alkyl groups may be substituted in any way.

[0031] As used in this specification, the term "cycloalkyl" 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, adamantyl, etc. Furthermore, cycloalkyl groups may be substituted in any way.

[0032] As used in this specification, the term "alkenyl" refers to both straight-chain alkenyl radicals and branched alkenyl radicals having one or more carbon-carbon double bonds. 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, etc. Furthermore, the alkenyl group can be arbitrarily substituted.

[0033] As used in this specification, the term "cycloalkenyl" refers to a cyclic alkenyl radical. Unless otherwise specified, a cycloalkenyl radical contains 3 to 20 carbon atoms, and furthermore, the cycloalkenyl radical can be arbitrarily substituted.

[0034] As used in this specification, the term "alkynyl" refers to both straight-chain alkynyl radicals and branched alkynyl radicals having one or more carbon-carbon triple bonds. Unless otherwise specified, an alkynyl radical contains 2 to 30 carbon atoms and may include, but is not limited to, ethynyl, 2-propynyl, etc. Furthermore, the alkynyl radical can be arbitrarily substituted.

[0035] As used in this specification, the term "cycloynyl" refers to a cyclic ynyl radical. Unless otherwise specified, a cycloynyl radical contains 3 to 20 carbon atoms, and furthermore, the cycloynyl radical can be arbitrarily substituted.

[0036] The terms “arylalkyl” or “aralkyl” used in this specification may be used interchangeably and refer to an alkyl group having an aromatic group as a substituent. Furthermore, arylalkyl (aralkyl) may be substituted in any way.

[0037] The terms "aryl" or "aromatic group" used in this specification have the same meaning, and aryl includes both monocyclic and polycyclic groups. Polycyclic groups can include "fused rings" consisting of two or more rings shared by two adjacent rings, with two carbon atoms. Furthermore, it can also include forms where two or more rings are simply linked or fused together. Unless otherwise specified, aryl groups contain 6 to 30 carbon atoms and can include, but are not limited to, phenyl, naphthyl, anthraceneyl, phenanthryl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, etc. Furthermore, aryl groups can be substituted in any way.

[0038] The terms "heteroaryl" or "heteroaromatic group" as used in this specification can be used interchangeably, and heteroaryl includes both monocyclic and polycyclic groups. Polycyclic groups can include "fused rings" of two or more rings shared by two adjacent rings, where two carbon atoms or heteroatoms are present. Furthermore, they can also include forms where two or more rings are simply linked or fused together. Unless otherwise specified, heteroaryl groups contain 5 to 60 carbon atoms; when there are 1 or 2 carbon atoms, rings can be formed by including additional heteroatoms. Furthermore, the heteroaryl group can contain 1 to 30 carbon atoms. In this case, more than one carbon atom in the ring is replaced by a heteroatom such as oxygen (O), nitrogen (N), sulfur (S), or selenium (Se). It can include 6-membered monocyclic rings, such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings, such as phenoxthioyl, indoleazinyl, indoleyl, purine, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, dibenzoxazolyl, dibenzothiazolyl, benzimidazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, phenylcarbazolyl, 9-phenylcarbazolyl, and carbazolyl; as well as 2-furanyl, N-imidazolyl, 2-isooxazolyl, 2-pyridinyl, and 2-pyrimidinyl, but is not limited thereto. Furthermore, the heteroaryl group can be arbitrarily substituted.

[0039] As used in this specification, the term "heterocyclic group" refers to a group in which one or more carbon atoms constituting an aryl, cycloalkyl, cycloalkenyl, cycloalkynyl, aralkyl, or arylamino group are substituted with heteroatoms such as oxygen (O), nitrogen (N), or sulfur (S). Referring to the definition, it includes heteroaryl, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, heteroarylalkyl, and heteroarylamino groups. Furthermore, heterocyclic groups can be substituted in any way.

[0040] Unless otherwise specified, the term "carbon ring" as used in this specification may be used as a term that includes both "cycloalkyl" as an alicyclic cyclic group and "aryl (aromatic group)" as an aromatic cyclic group.

[0041] As used in this specification, the terms "heteroalkyl" and "heteroaryl" mean that one or more carbon atoms constituting an alkyl or aryl group are replaced by heteroatoms such as oxygen (O), nitrogen (N), sulfur (S) or selenium (Se). Furthermore, heteroalkyl and heteroaryl groups can be substituted in any way.

[0042] As used in this specification, the terms "alkylamino", "arylalkylamino", "arylamino", and "heteroarylamino" refer to amino groups (or amino groups) that are substituted by the alkyl, arylalkyl, aryl, or heteroaryl groups, and simultaneously include primary, secondary, or tertiary amino groups (or amino groups). Furthermore, alkylamino, arylalkylamino, arylamino, and heteroarylamino groups can be substituted in any way.

[0043] The terms “alkylsilyl”, “arylsilyl”, “alkoxy”, “aryloxy”, “alkathio”, and “arylthio” used in this specification refer to the substitution of silyl, oxy, and thio groups by the alkyl and aryl groups, respectively. Furthermore, alkylsilyl, arylsilyl, alkoxy, aryloxy, alkathio, and arylthio can be substituted in any way.

[0044] As used in this specification, the terms "arylene," "arylalkylene," "heteroarylene," and "heteroarylalkylene" refer to the aryl, aralkyl, heteroaryl, and heteroaryl groups each comprising one or more divalent substituents. Furthermore, the arylene, arylalkylene, heteroarylene, and heteroarylalkylene groups may be substituted in any way.

[0045] As used in this specification, the term "substitution" means replacing the hydrogen (H) atom bonded to the carbon or nitrogen atom of the compound of the present invention with a substituent other than hydrogen. In the case of multiple substituents, the substituents may be the same as or different from each other.

[0046] The substituents are each independently selected from deuterium, trifluoromethyl, nitro, halogen group, hydroxyl, trimethylsilyl (TMS), alkyl with 1 to 30 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, alkenyl with 2 to 30 carbon atoms, cycloalkenyl with 3 to 20 carbon atoms, alkynyl with 2 to 30 carbon atoms, cycloalkynyl with 3 to 20 carbon atoms, aryl with 6 to 30 carbon atoms, aralkyl with 7 to 30 carbon atoms, heteroaryl with 5 to 60 carbon atoms, heteroaryl with 6 to 60 carbon atoms, amino, alkylamino with 1 to 30 carbon atoms, carbon atom The ring is substituted with one or more substituents from the group consisting of arylalkylamino with 7 to 30 carbon atoms, arylamino with 6 to 30 carbon atoms, heteroarylamino with 5 to 60 carbon atoms, silyl, alkylsilyl with 1 to 30 carbon atoms, arylsilyl with 6 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, aryloxy with 6 to 30 carbon atoms, alkylthio with 1 to 30 carbon atoms, and arylthio with 6 to 30 carbon atoms. When substituted with multiple substituents, they may be the same as or different from each other, and they may bond with adjacent groups to form substituted or unsubstituted rings.

[0047] Unless otherwise specified, the objects and substituents defined in this specification may be the same or different.

[0048] The organic compounds of the present invention and organic light-emitting devices comprising the same will be described in detail below.

[0049] The organic compounds of the present invention can be represented by the following chemical formula 1.

[0050] Chemical Formula 1:

[0051]

[0052] X represents oxygen (O) or sulfur (S).

[0053] Y1, Y2, and Y3 are nitrogen (N) or CR2.

[0054] At least two of Y1, Y2 and Y3 are nitrogen (N).

[0055] Z1, Z2, and Z3 are nitrogen (N) or CR3.

[0056] L1 and L2 may be the same as or different from each other, and are each independently selected from the group consisting of a direct bond, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group with 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 60 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group with 6 to 60 carbon atoms.

[0057] A is selected from the group consisting of alkyl groups with 1 to 30 carbon atoms (substituted or unsubstituted), cycloalkyl groups with 3 to 20 carbon atoms (substituted or unsubstituted), aryl groups with 6 to 30 carbon atoms (substituted or unsubstituted), aralkyl groups with 7 to 30 carbon atoms (substituted or unsubstituted), heteroaryl groups with 5 to 60 carbon atoms (substituted or unsubstituted), heteroarylalkyl groups with 6 to 60 carbon atoms (substituted or unsubstituted), aromatic amino groups with 6 to 30 carbon atoms (substituted or unsubstituted), arylalkylamino groups with 6 to 30 carbon atoms (substituted or unsubstituted), heteroarylamino groups with 5 to 60 carbon atoms (substituted or unsubstituted), arylsilyl groups with 6 to 30 carbon atoms (substituted or unsubstituted), and aryloxy groups with 6 to 30 carbon atoms (substituted or unsubstituted), and is capable of bonding with adjacent groups to form substituted or unsubstituted rings.

[0058] Ar1 and Ar2 may be the same as or different from each other, and are each independently selected from the group consisting of aryl groups with 6 to 30 carbon atoms (substituted or unsubstituted), aralkyl groups with 7 to 30 carbon atoms (substituted or unsubstituted), heteroaryl groups with 5 to 60 carbon atoms (substituted or unsubstituted), heteroarylalkyl groups with 6 to 60 carbon atoms (substituted or unsubstituted), arylamino groups with 6 to 30 carbon atoms (substituted or unsubstituted), arylalkylamino groups with 6 to 30 carbon atoms (substituted or unsubstituted), heteroarylamino groups with 5 to 60 carbon atoms (substituted or unsubstituted), arylsilyl groups with 6 to 30 carbon atoms (substituted or unsubstituted), and aryloxy groups with 6 to 30 carbon atoms (substituted or unsubstituted), and are capable of bonding with adjacent groups to form substituted or unsubstituted rings.

[0059] R1, R2, and R3 may be the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl groups with 6 to 60 carbon atoms, substituted or unsubstituted arylamino groups with 6 to 30 carbon atoms, substituted or unsubstituted arylalkylamino groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroarylamino groups with 5 to 60 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 30 carbon atoms, and substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, and are capable of bonding with adjacent groups to form substituted or unsubstituted rings.

[0060] p is an integer from 0 to 7.

[0061] The substituents of L1, L2, A, Ar1, Ar2, R1, R2, and R3 are each independently selected from deuterium, trifluoromethyl, nitro, halogen group, hydroxyl group, trimethylsilyl (TMS), alkyl with 1 to 30 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, alkenyl with 2 to 30 carbon atoms, cycloalkenyl with 3 to 20 carbon atoms, alkynyl with 2 to 30 carbon atoms, cycloalkynyl with 3 to 20 carbon atoms, aryl with 6 to 30 carbon atoms, aralkyl with 7 to 30 carbon atoms, heteroaryl with 5 to 60 carbon atoms, heteroaryl with 6 to 60 carbon atoms, amino, and groups with 1 to 30 carbon atoms. The substituent is one or more of the following groups: alkylamino with 30 carbon atoms, arylalkylamino with 7 to 30 carbon atoms, aromaticamino with 6 to 30 carbon atoms, heteroaromaticamino with 5 to 60 carbon atoms, silyl, alkylsilyl with 1 to 30 carbon atoms, arylsilyl with 6 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, aryloxy with 6 to 30 carbon atoms, alkylthio with 1 to 30 carbon atoms, and arylthio with 6 to 30 carbon atoms. When substituted by multiple substituents, they may be the same as or different from each other, and they may bond with adjacent groups to form substituted or unsubstituted rings.

[0062] According to an embodiment of the present invention, the direct bond or single bond refers to the direct bonding of structural elements of the chemical formula on both sides of L1 and L2, as if L1 and L2 were not present in the chemical formula.

[0063] According to one embodiment of the present invention, L1 and L2 may be the same as or different from each other, and may each be a direct bond or a divalent phenylene.

[0064] The direct bond refers to the direct bonding of structural elements of the chemical formulas on both sides of L1 and L2, just as in chemical formula 1 where L1 and L2 are not present. This can be confirmed by chemical formula 2-1, etc.

[0065] The divalent phenylene refers to a 6-position phenylene that can undergo substitution bonding, where two positions are substituted. This can be any of 1,2 (ortho) substitution, 1,3 (meta) substitution, or 1,4 (para) substitution, and can be selected from the structures described below. (In some of the compounds described below, * indicates a portion of the compound that is bonded by a single bond.)

[0066]

[0067] According to one embodiment of the present invention, Y1, Y2 and Y3 can be as follows.

[0068] -Y1 and Y2 are nitrogen, Y3 is CR2, and R2 is hydrogen;

[0069] -Y1 and Y3 are nitrogen, Y2 is CR2, and R2 is hydrogen;

[0070] -Y2 and Y3 are nitrogen, Y1 is CR1, and R1 is hydrogen;

[0071] -Y1, Y2 and Y3 are all nitrogen.

[0072] According to one embodiment of the present invention, A may be an alkyl group with 1 to 30 carbon atoms that is substituted or unsubstituted, a cycloalkyl group with 3 to 20 carbon atoms that is substituted or unsubstituted, or an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted.

[0073] According to one embodiment of the present invention, A may be substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazoleyl.

[0074] According to one embodiment of the present invention, Ar1 and Ar2 may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazoyl.

[0075] According to one embodiment of the present invention, the compound of chemical formula 1 may contain at least one deuterium.

[0076] According to one embodiment of the present invention, the organic compound of chemical formula 1 can be represented by the following chemical formula 2.

[0077] Chemical formula 2:

[0078]

[0079] The definitions of X, L1, L2, A, Ar1, Ar2, R1 and R2 and their substituents are the same as those in Chemical Formula 1.

[0080] According to one embodiment of the present invention, the organic compounds of chemical formula 1 and chemical formula 2 can be represented by the following chemical formulas 2-1 to 2-8.

[0081] In the following chemical formulas 2-1 to 2-8, 2-1-1 to 2-1-4, 2-2-1 to 2-2-4, 2-3-1 to 2-3-6, 2-4-1 to 2-4-6, 2-5-1 to 2-5-4, 2-6-1 to 2-6-4, 2-7-1 to 2-7-6, and 2-8-1 to 2-8-6, the definitions of X, A, Ar1, Ar2, R1, R2, and p and their substituents are the same as those in chemical formula 1.

[0082] Chemical formula 2-1:

[0083]

[0084] The 2-1 structure may include, but is not limited to, the following structures.

[0085]

[0086] Chemical formula 2-2:

[0087]

[0088] The 2-2 structure may include, but is not limited to, the following structures.

[0089]

[0090] Chemical formula 2-3:

[0091]

[0092] The structure described in section 2-3 may include, but is not limited to, the following structures.

[0093]

[0094] Chemical formula 2-4:

[0095]

[0096] The 2-4 structure may include, but is not limited to, the following structures.

[0097]

[0098] Chemical formula 2-5:

[0099]

[0100] The structures described in 2-5 may include, but are not limited to, the following structures.

[0101]

[0102] Chemical formula 2-6:

[0103]

[0104] The structures described in 2-6 may include, but are not limited to, the following structures.

[0105]

[0106] Chemical formula 2-7:

[0107]

[0108] The structures described in 2-7 may include, but are not limited to, the following structures.

[0109]

[0110] Chemical formula 2-8:

[0111]

[0112] The 2-8 structure may include, but is not limited to, the following structures.

[0113]

[0114] According to one embodiment of the present invention, the organic compound of chemical formula 1 can be represented by the following chemical formula 3.

[0115] Chemical formula 3:

[0116]

[0117] The definitions of X, L1, L2, A, Ar1, Ar2, R1, and R2 and their substituents are the same as those in Chemical Formula 1.

[0118] According to one embodiment of the present invention, the organic compounds of chemical formula 1 and chemical formula 3 can be represented by the following chemical formulas 3-1 to 3-8.

[0119] In the following chemical formulas 3-1 to 3-8, 3-1-1 to 3-1-4, 3-2-1 to 3-2-4, 3-3-1 to 3-3-6, 3-4-1 to 3-4-6, 3-5-1 to 3-5-4, 3-6-1 to 3-6-4, 3-7-1 to 3-7-6, and 3-8-1 to 3-8-6, the definitions of X, A, Ar1, Ar2, R1, R2, and p and their substituents are the same as those in chemical formula 1.

[0120] Chemical formula 3-1:

[0121]

[0122] The 3-1 structure may include, but is not limited to, the following structures.

[0123]

[0124] Chemical formula 3-2:

[0125]

[0126] The 3-2 structure may include, but is not limited to, the following structures.

[0127]

[0128] Chemical formula 3-3:

[0129]

[0130] The 3-3 structure may include, but is not limited to, the following structures.

[0131]

[0132] Chemical formula 3-4:

[0133]

[0134] The 3-4 structure may include, but is not limited to, the following structures.

[0135]

[0136] Chemical formula 3-5:

[0137]

[0138] The 3-5 structure may include, but is not limited to, the following structures.

[0139]

[0140] Chemical formula 3-6:

[0141]

[0142] The 3-6 structure may include, but is not limited to, the following structures.

[0143]

[0144] Chemical formula 3-7:

[0145]

[0146] The structures described in 3-7 may include, but are not limited to, the following structures.

[0147]

[0148] Chemical formula 3-8:

[0149]

[0150] The 3-8 structure may include, but is not limited to, the following structures.

[0151]

[0152] According to one embodiment of the present invention, the organic compound of chemical formula 1 can be represented by the following chemical formula 4.

[0153] Chemical formula 4:

[0154]

[0155] The definitions of X, L1, L2, A, Ar1, Ar2, R1, and R2 and their substituents are the same as those in Chemical Formula 1.

[0156] According to one embodiment of the present invention, the organic compounds of chemical formulas 1 and 4 can be represented by the following chemical formulas 4-1 to 4-8.

[0157] In the following chemical formulas 4-1 to 4-8, 4-1-1 to 4-1-4, 4-2-1 to 4-2-4, 4-3-1 to 4-3-6, 4-4-1 to 4-4-6, 4-5-1 to 4-5-4, 4-6-1 to 4-6-4, 4-7-1 to 4-7-6, and 4-8-1 to 4-8-6, the definitions of X, A, Ar1, Ar2, R1, R2, and p and their substituents are the same as those in chemical formula 1.

[0158] Chemical formula 4-1:

[0159]

[0160] The 4-1 structure may include, but is not limited to, the following structures.

[0161]

[0162] Chemical formula 4-2:

[0163]

[0164] The 4-2 structure may include, but is not limited to, the following structures.

[0165]

[0166] Chemical formula 4-3:

[0167]

[0168] The 4-3 structure may include, but is not limited to, the following structures.

[0169]

[0170] Chemical formula 4-4:

[0171]

[0172] The 4-4 structure may include, but is not limited to, the following structures.

[0173]

[0174] Chemical formula 4-5:

[0175]

[0176] The 4-5 structure may include, but is not limited to, the following structures.

[0177]

[0178] Chemical formula 4-6:

[0179]

[0180] The 4-6 structure may include, but is not limited to, the following structures.

[0181]

[0182] Chemical formula 4-7:

[0183]

[0184] The 4-7 structure may include, but is not limited to, the following structures.

[0185]

[0186] Chemical formula 4-8:

[0187]

[0188] The 4-8 structure may include, but is not limited to, the following structures.

[0189]

[0190] According to an embodiment of the present invention, in the chemical formulas 1, 2, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 3, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 4, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 4-7, and 4-8, L1 and L2 may be selected from compounds with structures A1 to A6. (In the following partial compounds, * refers to the portion of the compound that is bonded by single bonds.)

[0191]

[0192] According to an embodiment of the present invention, in the following chemical formulas: 1, 2, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 3, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 4, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 4-7, 4-8, A may be selected from compounds with structures B1 to B18. (In the following partial compounds, * indicates a portion of the compound bonded by single bonds.)

[0193]

[0194]

[0195] According to an embodiment of the present invention, in the chemical formulas 1, 2, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 3, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 4, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 4-7, and 4-8, Ar1 and Ar2 can be selected from compounds with structures M1 to M32. (In some of the compounds described below, * indicates a portion of the compound bonded by single bonds.)

[0196]

[0197]

[0198] According to one embodiment of the present invention, the compound represented by chemical formula 1 may be selected from the group consisting of structures 1 to 82, Tables 1 to 24, and deuterium compound structures 1919 to 1927, but is not limited thereto.

[0199]

[0200]

[0201]

[0202] Table 1

[0203]

[0204]

[0205] Table 2

[0206]

[0207]

[0208] Table 3

[0209]

[0210]

[0211] Table 4

[0212]

[0213]

[0214] Table 5

[0215]

[0216]

[0217] Table 6

[0218]

[0219]

[0220] Table 7

[0221]

[0222]

[0223] Table 8

[0224]

[0225]

[0226] Table 9

[0227]

[0228]

[0229] Table 10

[0230]

[0231]

[0232] Table 11

[0233]

[0234]

[0235] Table 12

[0236]

[0237]

[0238] Table 13

[0239]

[0240]

[0241] Table 14

[0242]

[0243]

[0244] Table 15

[0245]

[0246]

[0247] Table 16

[0248]

[0249]

[0250] Table 17

[0251]

[0252]

[0253] Table 18

[0254]

[0255]

[0256] Table 19

[0257]

[0258]

[0259] Table 20

[0260]

[0261]

[0262] Table 21

[0263]

[0264]

[0265] Table 22

[0266]

[0267]

[0268] Table 23

[0269]

[0270]

[0271] Table 24

[0272]

[0273]

[0274]

[0275] The organic light-emitting device of the present invention may include: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic layers located inside the first electrode and the second electrode, wherein at least one of the organic layers may contain the compound represented by chemical formula 1.

[0276] The organic light-emitting device may include one or more of the following layers as organic layers: 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; it may also include a charge generation layer, a hole transport auxiliary layer, a light-emitting auxiliary layer, an electron transport auxiliary layer, etc.

[0277] 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 stacked sequentially.

[0278] The organic light-emitting device of this invention may include an electron transport layer or an electron transport auxiliary layer comprising a compound represented by chemical formula 1.

[0279] The organic light-emitting device described in this embodiment of the invention may further include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection layer.

[0280] For example, the first electrode may contain transparent and highly conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO).

[0281] The hole injection layer or hole transport layer compound is not particularly limited, and any compound commonly used as a hole injection layer or hole transport layer compound can be used. Non-limiting examples of hole injection layer or hole transport layer compounds may include phthalocyanine derivatives, porphyrin derivatives, triarylamine derivatives, and indolecarbazole derivatives. Examples include 1,4,5,8,9,11-hexaazatriphenylhexanitrile (HAT-CN), copper phthalocyanine (CuPc), 4,4',4”-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4”-tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), 4,4',4”-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2-TNATA), N4,N4,N4',N4'-tetra([1,1'-bi [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'-bis(naphthyl-1-yl)-N,N'-biphenyl-benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), etc.

[0282] The compounds contained in the light-emitting layer are not particularly limited; any compound commonly used as a light-emitting layer compound can be used, and either a single light-emitting compound or a light-emitting host compound can be used.

[0283] The luminescent compound serving as the luminescent layer may include, but is not limited to, compounds capable of emitting phosphorescence, fluorescence, thermal ignition delayed fluorescence (TADF, or also known as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes to achieve luminescence. Depending on the desired luminescence color, the luminescent compound can be selected from a variety of materials. Non-limiting examples of luminescent compounds may include phenanthrene, anthracene, pyrene, tetraphenyl, pentaphenyl, perylene, naphthopyrene, dibenzopyrene, fluorene and pyroxene, fused-ring derivatives such as 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, bis(styrene) derivatives, bis(styrene) aromatic derivatives, diazaindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives, dibenzofuran derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethimide derivatives, and anthocyanin derivatives. Derivatives include oxobenzoxanthracene derivatives, xanthones, rhodamine derivatives, fluorescein derivatives, pyranonium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenyl ether derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furanopyridine derivatives, 1,2,5-thiadiazopyrene derivatives, pyrrole methylene derivatives, pyrene derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridineone derivatives, desoxyflavin derivatives, fluorene derivatives, benzo[a]fluorene derivatives, aromatic boron derivatives, aromatic nitrogen boron derivatives, and metal complexes (complexes formed by metals such as Ir, Pt, Au, Eu, Ru, Re, Ag, and Cu with heterocyclic aromatic ligands, etc.).Examples include N1,N1,N6,N6-tetrakis(4-(1-methylyl)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-boronazonaphtho[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), and 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)3·2(PF6), Ir(BT)2(acac), Ir(DMP)3, Ir(Mp hq)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, FIrpic, etc.

[0284] The host compound for the luminescent layer can be a luminescent host, a hole-transporting host, an electron-transporting host, or a combination thereof. Non-limiting examples of luminescent host compounds may include fused-ring derivatives such as anthracene or pyrene, bis(5-phenylene)-anthracene derivatives or stilbene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzo[a]fluorene derivatives, N-phenylcarbazole derivatives, carbazole nitrile derivatives, etc. Non-limiting examples of hole-transporting host substances may include carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, triarylamine derivatives, indolecarbazole derivatives, and benzo[a]oxazinophenazine derivatives, etc. Non-limiting examples of electron-transporting host substances may include pyridine derivatives, triazine derivatives, phosphine oxide derivatives, benzo[a]furan-pyridine derivatives, and dibenzo[a]oxazolidinyl derivatives. Examples include 9,10-bis(2-naphthyl)anthracene (ADN), tris(8-hydroxyquinoline)aluminum (Alq3), BAlq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis(2,2-bistyryl)-1,1'-biphenyl) series, spiro-DPVBi (spiro-4,4'-bis(2,2-bistyryl)-1,1'-biphenyl), LiPBO (2-(2-benzoxazolyl)phenol lithium salt), bis(bistyryl)benzene, aluminum-quinoline metal complexes, imidazole, thiazole and oxazole metal complexes, etc.

[0285] An electron blocking layer (EBL) may also 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 can be used. For example, the electron blocking layer may include N-phenyl-N-(4-(spiro[benzo[d,e]anthracene-7,9'-fluorene]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine), etc.

[0286] An electron transport auxiliary layer may be formed between the light-emitting layer and the electron transport layer. The electron transport auxiliary layer compound is not particularly limited, and any compound commonly used as an electron transport auxiliary layer compound can be used. For example, the electron transport auxiliary layer may include 2-[3'-(9,9-dimethyl-9H-fluorene-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine, etc.

[0287] The electron injection layer, electron transport layer, electron transport auxiliary layer, or hole blocking layer compound is not particularly limited, and any compound commonly used as an electron injection layer, electron transport layer, electron transport auxiliary layer, or hole blocking layer compound may be used. Non-limiting examples of electron injection layer or electron transport layer compounds may include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, violet ketone derivatives, coumarin derivatives, naphthylimide derivatives, anthraquinone derivatives, dibenzoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, metal complexes of oxime derivatives, quinoline metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzo[a]azole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, and triazine derivatives. Pyrazine derivatives, benzoquinoline derivatives, imidazopyridine derivatives, borane derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives, naphthidine derivatives, aldehyde azide derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bis(5-phenylene oxide) metal complexes, quinoline alcohol metal complexes, hydroxyazole metal complexes, azomethyl alkaloid metal complexes, tyrosine metal complexes, flavonol metal complexes, benzoquinoline metal complexes, metal salts, etc. These materials can be used alone or in combination with other materials. For example, they may include 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, tris(8-hydroxyquinoline)aluminum (Alq3), LiF, Liq, Li2O, BaO, NaCl, CsF, etc.

[0288] The second electrode (cathode) can contain materials such as lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). Furthermore, in the case of top-emitting organic light-emitting devices, indium tin oxide (ITO) or indium zinc oxide (IZO) can be used to form a transparent cathode that allows light to pass through.

[0289] The organic light-emitting device in this embodiment of the invention can be either top-emitting or bottom-emitting.

[0290] The organic light-emitting device of this invention can be used in display devices.

[0291] The organic light-emitting devices of the present invention can be applied to transparent display devices, mobile display devices, flexible display devices, etc., but are not limited thereto.

[0292] The following examples illustrate the method for synthesizing the compounds. However, the method for synthesizing the compounds of the present invention is not limited to the methods described in the examples below.

[0293] The definitions of X, Y1, Y2, Y3, L1, L2, A, Ar1, Ar2, R1, and R2 recorded in SUB 1, SUB 2, SUB 3, SUB 4, and Product are the same as those in Chemical Formula 1.

[0294] In the following reaction formula, Halogen represents a halogen group, but the equivalent Halogen group can be used.

[0295] In the following reaction formula, "boronic compound" refers to boric acid, borate esters, dioxoborane, etc., but any equivalent "boronic compound" can be used.

[0296] In the following reaction formulas, solvents, catalysts, etc. are representative examples, and any equivalent solvents, catalysts, etc. can be used.

[0297] Synthesis example

[0298] 1. Synthesize SUB 3

[0299] SUB 3 can be synthesized as follows, but is not limited to these.

[0300] Reaction 1

[0301]

[0302] Under a nitrogen atmosphere, SUB 1 (44 mmol, 5.4 g), SUB 2 (40 mmol, 21.7 g), K₂CO₃ (120 mmol, 16.6 g), Pd(PPh₃)₄ (1.6 mmol, 4.6 g), 1,4-Dioxane (440 mL), and water (88 mL) were added to a 1000 mL flask and stirred under reflux for 24 hours. After the reaction was complete, the organic layer was extracted with CH₂Cl₂ and water. The extracted solution was treated with MgSO₄ to remove residual water, concentrated under reduced pressure, purified by column chromatography, and recrystallized to give 19.4 g of the following SUB 3-6. (Yield: 90%) m / z = 538.10 (C₃₄H₂₃BrN₂ = 539.48)

[0303] Representative synthesized SUB 3 compounds are shown in Table 25 below. SUB 3 compounds for specific compounds of the present invention and similar compounds can be synthesized with reference to the synthesis examples described herein.

[0304] Table 25

[0305]

[0306]

[0307]

[0308]

[0309] 2. Synthetic Product

[0310] The product can be synthesized as follows, but is not limited to these methods.

[0311] Reaction 2

[0312]

[0313] Under a nitrogen atmosphere, SUB 3 (20 mmol, 10.8 g), SUB 4 (22 mmol, 5.4 g), K₂CO₃ (60 mmol, 8.3 g), Pd(PPh₃)₄ (0.8 mmol, 0.9 g), 1,4-dioxane (110 mL), and water (22 mL) were added to a 250 mL flask and stirred under reflux for 24 hours. After the reaction was complete, the organic layer was extracted with CH₂Cl₂ and water. The extracted solution was treated with MgSO₄ to remove residual water, concentrated under reduced pressure, purified by column chromatography, and recrystallized to give 9.8 g of compound 2 as the product. (Yield: 78%) m / z = 626.24 (C₃₄H₂₃BrN₂ = 626.76)

[0314] Representative synthesized compounds are shown in Table 26 below. Specific compounds of the present invention and similar compounds can be synthesized with reference to the synthetic examples described herein.

[0315] Table 26

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324] Experiment Example 1: Simulation Results

[0325] Experimental Example 1: Simulation Results of Electron Transport Auxiliary Layer

[0326] The electron transport auxiliary layer serves to reduce hole leakage at the interface of the light-emitting layer due to the LUMO energy level difference between the electron transport layer and the light-emitting layer. Therefore, it is preferable that the LUMO energy level difference with the light-emitting layer is greater than the LUMO energy level difference with the electron transport layer.

[0327] Table 27

[0328]

[0329] Experimental Example 2: Simulation Results of Electron Transport Layer

[0330] The electron transport layer has a suitable LUMO energy level between the electron transport auxiliary layer and the electron injection layer, or between the light-emitting layer (in the absence of an electron transport auxiliary layer) and the electron injection layer, thereby playing the role of transferring electrons to the electron transport auxiliary layer or the light-emitting layer (in the absence of an electron transport auxiliary layer). For this purpose, it is preferable that the LUMO energy level difference with the electron transport auxiliary layer or the light-emitting layer (in the absence of an electron transport auxiliary layer) is smaller than the LUMO energy level difference with the electron injection layer.

[0331] Table 28

[0332]

[0333] Experimental Example 3: Experimental Results of Electron Transport Auxiliary Layer Device

[0334] A substrate with ITO (100nm) layered on top as the anode of an organic electroluminescent device is divided into a cathode region, an anode region, and an insulating layer by a photolithography process and patterned. Then, in order to improve the work function of the anode (ITO) and to clean it, the surface is treated with ultraviolet (UV)-ozone and O2:N2 plasma.

[0335] Then, 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) is deposited on the anode to form a 10 nm thick hole injection layer (HIL).

[0336] Next, a 90 nm thick hole transport layer is formed by vacuum deposition of 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) on top of the hole injection layer. A 15 nm thick electron blocking layer (EBL) is formed by accumulating N-phenyl-N-(4-(spiro[benzo[d,e]anthracene-7,9'-fluorene]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine.

[0337] A 25 nm thick layer of 9,10-bis(2-naphthyl)anthracene (ADN) was deposited on top of the electron blocking layer (EBL) as the host, and about 3 wt% of 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) was used as a dopant. As shown in Table 29 below, the compounds of the present invention are vacuum deposited to form an electron transport auxiliary layer with a thickness of 5 nm for the light-emitting layer. A mixture of 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (2-(4-(9,10-Di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and Liq in a 1:1 weight ratio is deposited on the electron transport auxiliary layer as an electron transport layer. A 1 nm thick layer of Liq is deposited on the electron transport layer as an electron injection layer, and a 100 nm thick layer of aluminum is deposited as a cathode. A 60 nm thick layer of N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited on the cathode as a capping layer.

[0338] Next, a seal cap is bonded to the cover layer (CPL) using an ultraviolet (UV) curable adhesive, which protects the organic light-emitting device from atmospheric oxygen (O2) or moisture, thereby fabricating the organic light-emitting device.

[0339] Except for using the compounds in Table 29 and the comparative compounds 1 and 2 below instead of the compounds in Example 1 below as electron transport auxiliary layers, Examples 2 to 10 and Comparative Examples 1 and 2 were prepared in the same manner as in Example 1.

[0340]

[0341] For the organic light-emitting devices of Examples 2 to 10 and Comparative Examples 1 and 2, a CS-2000 from Konica Minolta was used to apply 10 mA / cm². 2 The driving voltage (Op V) and efficiency (Cd / A) were measured using the current, and McScience's M6000 was used at 10 mA / cm². 2 The constant current drive confirmed the method of determining lifetime (LT95) by reducing the brightness time from the initial brightness to 95% level.

[0342] The measurement results are shown in Table 29 below.

[0343] Table 29

[0344]

[0345] Referring to Table 29, the compound of the present invention is a blue OLED device material, which can be confirmed to have high efficiency and long lifespan.

[0346] In the case of the comparative compound, it was confirmed that the device efficiency and lifetime were significantly reduced.

[0347] Experiment Example 4: Experimental Results of Electron Transport Layer Devices

[0348] A substrate with ITO (100nm) layered on top as the anode of an organic electroluminescent device is divided into a cathode region, an anode region, and an insulating layer by a photolithography process and patterned. Then, in order to improve the work function of the anode (ITO) and to clean it, the surface is treated with ultraviolet (UV)-ozone and O2:N2 plasma.

[0349] Then, 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) is deposited on the anode to form a 10 nm hole injection layer (HIL).

[0350] Next, a 90 nm thick hole transport layer is formed by vacuum deposition of 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) on top of the hole injection layer. N-Phenyl-N-(4-(spiro[benzo[d,e]anthracene-7,9'-fluorene]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine is used to form a 15 nm thick electron blocking layer (EBL).

[0351] A 25 nm thick layer of 9,10-bis(2-naphthyl)anthracene (ADN) was deposited on top of the electron blocking layer (EBL) as the host, and about 3 wt% of 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) was used as a dopant. Vacuum deposition of 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine (2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine) was used to form a 5 nm thick electron transport auxiliary layer for the light-emitting layer. A 25 nm thick compound from Table 30 below was deposited on the electron transport auxiliary layer as an electron transport layer (ETL). A 1 nm thick LiQ layer was deposited on the electron transport auxiliary layer as an electron injection layer. A 100 nm thick aluminum layer was deposited as a cathode. A 60 nm thick layer of N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited on the cathode as a capping layer.

[0352] Next, a seal cap is bonded to the cover layer (CPL) using an ultraviolet (UV) curable adhesive, which protects the organic light-emitting device from atmospheric oxygen (O2) or moisture, thereby fabricating the organic light-emitting device.

[0353] Except for using the compounds in Table 30 and the comparative compounds 3 and 4 below instead of the compounds in Example 11 below as electron transport auxiliary layers, Examples 11 to 112 and Comparative Examples 3 and 4 were prepared in the same manner as in Example 30.

[0354]

[0355] For the organic light-emitting devices of Examples 11 to 112 and Comparative Examples 3 and 4, the CS-2000 from Konica Minolta was tested by applying 10 mA / cm². 2 The driving voltage (Op V) and efficiency (Cd / A) were measured using the current, and McScience's M6000 was used at 10 mA / cm². 2 The constant current drive confirmed the method of determining lifetime (LT95) by reducing the brightness time from the initial brightness to 95% level.

[0356] The measurement results are shown in Table 30 below.

[0357] Table 30

[0358]

[0359]

[0360]

[0361]

[0362]

[0363] Referring to Table 30, the compound of the present invention is a blue OLED device material, and it can be confirmed that it has high efficiency and long lifespan.

[0364] In the case of the comparative compound, it was confirmed that the device efficiency and lifetime were significantly reduced.

[0365] The embodiments of the present invention have been described in detail above, but the scope of the claims of the present invention is not limited thereto. Various modifications and improvements made by those skilled in the art using the basic concepts of the present invention as defined in the following claims also fall within the scope of protection of the claims of the present invention.

Claims

1. An organic compound represented by the following chemical formula 1, characterized in that, Chemical Formula 1: ， X is oxygen or sulfur. Y1, Y2, and Y3 are nitrogen or CR2. At least two of Y1, Y2, and Y3 are nitrogen. Z1, Z2, and Z3 are nitrogen or CR3. L1 and L2 may be the same as or different from each other, and are each independently selected from the group consisting of a direct bond, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group with 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group with 5 to 60 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group with 6 to 60 carbon atoms. A is selected from the group consisting of alkyl groups with 1 to 30 carbon atoms (substituted or unsubstituted), cycloalkyl groups with 3 to 20 carbon atoms (substituted or unsubstituted), aryl groups with 6 to 30 carbon atoms (substituted or unsubstituted), aralkyl groups with 7 to 30 carbon atoms (substituted or unsubstituted), heteroaryl groups with 5 to 60 carbon atoms (substituted or unsubstituted), heteroarylalkyl groups with 6 to 60 carbon atoms (substituted or unsubstituted), aromatic amino groups with 6 to 30 carbon atoms (substituted or unsubstituted), arylalkylamino groups with 6 to 30 carbon atoms (substituted or unsubstituted), heteroarylamino groups with 5 to 60 carbon atoms (substituted or unsubstituted), arylsilyl groups with 6 to 30 carbon atoms (substituted or unsubstituted), and aryloxy groups with 6 to 30 carbon atoms (substituted or unsubstituted), and is capable of bonding with adjacent groups to form substituted or unsubstituted rings. Ar1 and Ar2 may be the same as or different from each other, and are each independently selected from the group consisting of aryl groups with 6 to 30 carbon atoms (substituted or unsubstituted), aralkyl groups with 7 to 30 carbon atoms (substituted or unsubstituted), heteroaryl groups with 5 to 60 carbon atoms (substituted or unsubstituted), heteroarylalkyl groups with 6 to 60 carbon atoms (substituted or unsubstituted), arylamino groups with 6 to 30 carbon atoms (substituted or unsubstituted), arylalkylamino groups with 6 to 30 carbon atoms (substituted or unsubstituted), heteroarylamino groups with 5 to 60 carbon atoms (substituted or unsubstituted), arylsilyl groups with 6 to 30 carbon atoms (substituted or unsubstituted), and aryloxy groups with 6 to 30 carbon atoms (substituted or unsubstituted), and are capable of bonding with adjacent groups to form substituted or unsubstituted rings. R1, R2, and R3 may be the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl groups with 6 to 60 carbon atoms, substituted or unsubstituted arylamino groups with 6 to 30 carbon atoms, substituted or unsubstituted arylalkylamino groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroarylamino groups with 5 to 60 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 30 carbon atoms, and substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, and are capable of bonding with adjacent groups to form substituted or unsubstituted rings. p is an integer from 0 to 7. The substituents of L1, L2, A, Ar1, Ar2, R1, R2, and R3 are each independently selected from deuterium, trifluoromethyl, nitro, halogen group, hydroxyl group, trimethylsilyl, alkyl with 1 to 30 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, alkenyl with 2 to 30 carbon atoms, cycloalkenyl with 3 to 20 carbon atoms, alkynyl with 2 to 30 carbon atoms, cycloalkynyl with 3 to 20 carbon atoms, aryl with 6 to 30 carbon atoms, aralkyl with 7 to 30 carbon atoms, heteroaryl with 5 to 60 carbon atoms, heteroaryl with 6 to 60 carbon atoms, amino, and groups with 1 to 30 carbon atoms. The substituted group is composed of one or more substituents from the group consisting of alkylamino, arylalkylamino with 7 to 30 carbon atoms, aromaticamino with 6 to 30 carbon atoms, heteroaromaticamino with 5 to 60 carbon atoms, silyl, alkylsilyl with 1 to 30 carbon atoms, arylsilyl with 6 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, aryloxy with 6 to 30 carbon atoms, alkylthio with 1 to 30 carbon atoms, and arylthio with 6 to 30 carbon atoms. When substituted by multiple substituents, they may be the same as or different from each other, and they may bond with adjacent groups to form substituted or unsubstituted rings.

2. The organic compound according to claim 1, characterized in that, Chemical formula 1 is represented by one of the following chemical formulas 2 to 4: Chemical formula 2: ， Chemical formula 3: ， Chemical formula 4: ， In the chemical formulas 2 to 4, The definitions of X, L1, L2, A, Ar1, Ar2, R1, and p and their substituents are the same as those in Formula 1.

3. An organic light-emitting device, characterized in that, include: First electrode; The second electrode is disposed opposite to the first electrode; and One or more organic layers are located between the first electrode and the second electrode. At least one of the organic layers comprises the organic compound according to claim 1.

4. The organic light-emitting device according to claim 3, characterized in that, The organic layer comprising the organic compound according to claim 1 is an electron transport auxiliary layer or an electron transport layer.

5. The organic light-emitting device according to claim 4, characterized in that, The organic layer further includes one or more selected from hole injection layer, hole transport layer, light emission layer and electron injection layer.

Images