Organic light emitting device comprising an organic compound

Abstract

The present specification relates to an organic light emitting device including a light emitting layer and a first organic layer.

Description

Technical Field

[0001] This specification relates to organic light-emitting devices that contain organic compounds.

[0002] This application claims priority to Korean Patent Application No. 10-2020-0105382, filed with the Korean Patent Office on August 21, 2020, the entire contents of which are contained in this specification. Background Technology

[0003] Organic light emission (OLED) typically refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices generally have a structure comprising an anode and a cathode, with an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials; for example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, they form excitons. When these excitons re-enter the ground state, they emit light.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the Invention

[0005] Technical issues

[0006] This specification provides organic light-emitting devices that contain organic compounds.

[0007] Solution to the problem

[0008] This specification provides an organic light-emitting device, comprising:

[0009] Anode, cathode, and an organic layer disposed between the anode and cathode.

[0010] The aforementioned organic layer includes a light-emitting layer and a first organic layer.

[0011] The first organic layer is disposed between the cathode and the light-emitting layer.

[0012] The aforementioned light-emitting layer comprises a compound of the following chemical formula 1,

[0013] The first organic layer described above contains a compound of the following chemical formula 2.

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0018] Ar1 and Ar2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0019] D stands for deuterium.

[0020] [Chemical Formula 2]

[0021]

[0022] In the above chemical formula 2,

[0023] L3 to L5 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0024] Ar3 and Ar4 may be the same as or different from each other, and each can be independently a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0025] Ar5 can be hydrogen, deuterium, cyano, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0026] At least one of Ar3 to Ar5 is a cyano group, or it contains one or more cyano groups as substituents.

[0027] n1 is an integer from 0 to 7.

[0028] Invention Effects

[0029] The organic light-emitting device described in this specification exhibits low driving voltage, excellent efficiency, and excellent lifetime by including a compound of Formula 1 in the light-emitting layer and a compound of Formula 2 in the first organic layer. Specifically, by appropriately adjusting the HOMO and LUMO energy levels to regulate electron transport, low driving voltage, high efficiency, and improved lifetime can be achieved. Attached Figure Description

[0030] Figure 1 , 2 Figure 8 illustrates an example of an organic light-emitting device according to one embodiment of this specification.

[0031] Figures 3 to 7 An example of an organic light-emitting device containing more than two stacked bodies is illustrated.

[0032] [Symbol Explanation]

[0033] 1: Substrate / 2: Anode / 3: Hole injection layer / 4: Hole transport layer / 4a: First hole transport layer / 4b: Second hole transport layer / 4c: Third hole transport layer / 4d: Fourth hole transport layer / 4e: Fifth hole transport layer / 4f: Sixth hole transport layer / 4p: P-doped hole transport layer / 4pa: First P-doped hole transport layer / 4R: Red hole transport layer / 4G: Green hole transport layer / 4B: Blue hole transport layer / 5: Electron blocking layer / 6: Light emitting layer / 6a: First light emitting layer / 6b: Second light emitting layer / 6c: Third light emitting layer / 6BF: Blue fluorescent light emitting layer / 6BFa: First blue fluorescent light emitting layer Layer / 6BFb: Second blue phosphorescent layer / 6BFc: Third blue phosphorescent layer / 6YGP: Yellow-green phosphorescent layer / 6RP: Red phosphorescent layer / 6GP: Green phosphorescent layer / 7: Hole blocking layer / 8: Electron injection and transport layer / 9a: First electron transport layer / 9b: Second electron transport layer / 9c: Third electron transport layer / 10: Electron injection layer / 11: Cathode / 12: N-type charge generation layer / 12a: First N-type charge generation layer / 12b: Second N-type charge generation layer / 13: P-type charge generation layer / 13a: First P-type charge generation layer / 13b: Second P-type charge generation layer / 14: Capping layer Detailed Implementation

[0034] The following is a more detailed description of this instruction manual.

[0035] The chemical formula 1 of the present invention has deuterium attached to carbons 1 to 8 of anthracene. In the recombination region within the light-emitting layer, it exhibits higher chemical stability compared to hydrogen, thereby improving the lifespan of organic light-emitting devices.

[0036] In the present invention, chemical formula 2 has a cyano substituent attached to anthracene, which increases the intramolecular dipole moment and thus enhances the electron injection effect.

[0037] When the compound of Chemical Formula 1 is used in the light-emitting layer and the compound of Chemical Formula 2 is used in the first organic layer (specifically the electron transport region), the device's long lifespan, low voltage, and high efficiency are enhanced.

[0038] The compounds of chemical formula 1 and the compounds of chemical formula 2 satisfy the following formula 1.

[0039] [Formula 1]

[0040] |DM2-DM1| ≥ 3 Debye

[0041] In Equation 1 above,

[0042] DM1 is the dipole moment of the compound of chemical formula 1 above.

[0043] DM2 is the dipole moment of the compound of chemical formula 2 above.

[0044] When Equation 1 is satisfied, electron injection from the cathode into the compound of Formula 2 is effectively generated, thereby allowing electron transfer to the light-emitting layer to be appropriately maintained. Therefore, the efficiency and lifetime of the organic light-emitting device are improved.

[0045] In this specification, dipole moment is a physical quantity that indicates the degree of polarity and can be calculated by the following mathematical formula 1.

[0046] [Mathematical Expression 1]

[0047]

[0048] In the above mathematical formula 1, the value of the dipole moment can be obtained by calculating the molecular density. For example, the molecular density can be calculated according to the following formula after determining the charge and dipole of each atom using a method called Hirshfeld Charge Analysis.

[0049]

[0050] According to one embodiment of this specification, the aforementioned dipole moment value can be calculated using Gaussian 03, a quantum chemical calculation program manufactured by Gaussian Corporation. Specifically, the dipole moment can be calculated using time-dependent density functional theory (TD-DFT) for a structure optimized using B3LYP as the functional and 6-31G* as the basis function.

[0051] In one embodiment of this specification, |DM2-DM1| of Formula 1 above is 6.5 Debye or less.

[0052] In this specification, * or dashed lines indicate connection points.

[0053] In this specification, Cn refers to a number of carbon atoms of n, and Cn-Cm refers to a number of carbon atoms from n to m.

[0054] Examples of substituents in this specification are described below, but are not limited thereto.

[0055] The term "substitution" refers to the replacement of hydrogen atoms on carbon atoms in a compound with other substituents. There is no limitation on the position of substitution, as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0056] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, cyano, alkyl, aryl and heterocyclic groups, or substituted by a substituent formed by linking two or more substituents of the substituents exemplified above, or having no substituents.

[0057] In this specification, the connection of two or more substituents means that the hydrogen of any one substituent is replaced by another substituent. For example, isopropyl can be connected to phenyl to form... or Such substituents.

[0058] In this specification, the connection of three substituents includes not only a continuous connection of (substituent 1)-(substituent 2)-(substituent 3), but also a connection of (substituent 2) and (substituent 3) within (substituent 1). For example, the connection of two phenyl groups and an isopropyl group can form... or Such substituents. The same definition applies to cases where four or more substituents are connected.

[0059] In this specification, N% deuteration means that N% of the usable hydrogens in the structure are replaced by deuterium. For example, in dibenzofuran, 25% deuteration means that 2 out of the 8 hydrogens in dibenzofuran are replaced by deuterium.

[0060] Compounds of Formula 1 containing deuterium can be produced by known deuteration reactions. According to one embodiment of this specification, compounds of Formula 1 can be formed by using a deuterated compound as a precursor, or deuterium can be introduced into the compound via a hydrogen-deuterium exchange reaction using a deuterated solvent and an acid catalyst.

[0061] In this specification, the degree of deuteration can be determined by nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 The results were confirmed using known methods such as H NMR or GC / MS.

[0062] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0063] In this specification, alkyl groups can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30, 1 to 20, 1 to 10, or 1 to 5. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0064] In this specification, silane can be alkylsilane or arylsilane, etc. Specifically, it can be represented by the chemical formula -SiYaYbYc, where Ya, Yb, and Yc can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. When Ya, Yb, and Yc are each alkyl, the silane is trialkylsilane; when Ya, Yb, and Yc are each aryl, the silane is triarylsilane. Specific examples of silane include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited to these.

[0065] In this specification, aryl refers to a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative. An aromatic hydrocarbon is a compound containing a planar ring with fully conjugated π electrons, and a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is fused together. Furthermore, in this specification, aryl includes a monovalent group formed by two or more aromatic hydrocarbons or aromatic hydrocarbon derivatives linked together. There is no particular limitation on the aryl group, but it is preferably an aryl group with 6 to 50, 6 to 30, 6 to 25, 6 to 20, 6 to 18, or 6 to 13 carbon atoms, and the aforementioned aryl group can be monocyclic or polycyclic. Specifically, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. As a polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, peryl, thionyl, fluorene, etc., but is not limited to these.

[0066] In this specification, the fluorene group can be substituted, and adjacent substituents can combine with each other to form a ring.

[0067] In this specification, when it is indicated that the fluorene group can be substituted, all compounds in which the substituents of the five-membered ring of fluorene are spirolinked together to form an aromatic hydrocarbon ring are included. The aforementioned substituted fluorene groups include, but are not limited to, 9,9'-spirodifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc.

[0068] In this specification, the substituted aryl group may also include a form in which an aliphatic ring is fused within the aryl group.

[0069] In this specification, a heterocyclic group refers to a monovalent aromatic heterocycle. Here, an aromatic heterocycle, as a monovalent group of an aromatic ring or a derivative of an aromatic ring, refers to a group containing one or more of N, O, and S as heteroatoms within the ring. The aforementioned aromatic ring derivatives include all structures in which aromatic rings or aliphatic rings are fused together. Furthermore, in this specification, a heterocyclic group comprises a monovalent group formed by the linkage of two or more aromatic rings containing heteroatoms or derivatives of aromatic rings containing heteroatoms. The number of carbon atoms in the aforementioned heterocyclic group is preferably 2 to 50, 2 to 30, 2 to 20, 2 to 18, or 2 to 13. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. Azolyl, pyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] The group includes, but is not limited to, azole, benzimidazole, benzothiazolyl, benzocarbazolyl, benzothiophene, dibenzothiophene, benzofuran, phenanthrolinel, and dibenzofuran.

[0070] In this specification, the heterocyclic group can be monocyclic or polycyclic, and can be aromatic, aliphatic, or a fused ring of aromatic and aliphatic compounds.

[0071] In this specification, cycloalkyl groups are not particularly limited, but are preferably cycloalkyl groups with 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Cycloalkyl groups include not only monocyclic groups, but also bicyclic groups such as bridgeheads, fused rings, and spiro rings. Specifically, they include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., but are not limited to these.

[0072] In this specification, aliphatic hydrocarbon rings refer to all hydrocarbon rings other than aromatic hydrocarbon rings, and may include cycloalkanes and cycloalkenes. Cycloalkanes, except that they are divalent groups, are subject to the above description regarding cycloalkyl groups, and cycloalkenes, except that they are divalent groups, are subject to the above description regarding cycloalkenyl groups. Furthermore, substituted aliphatic hydrocarbon rings also include aliphatic hydrocarbon rings fused with aromatic rings.

[0073] In this specification, arylene refers to a group with two bonding positions in an aryl group, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the same descriptions of aryl groups as described above.

[0074] In this specification, a heteroaryl group refers to a group with two bonding sites in a heterocyclic group, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the above description of heterocyclic groups.

[0075] The following is a detailed description of the compounds of chemical formula 1.

[0076] [Chemical Formula 1]

[0077]

[0078] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0079] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C2-C60 divalent heterocyclic group.

[0080] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 divalent heterocyclic group.

[0081] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene.

[0082] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a C6-C30 aryl group that is directly bonded, or substituted with deuterium, or unsubstituted.

[0083] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a C6-C20 aryl group that is directly bonded, or substituted with deuterium, or unsubstituted.

[0084] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each independently is a directly bonded, deuterated or unsubstituted phenylene, a deuterated or unsubstituted biphenylene, or a deuterated or unsubstituted naphthylene.

[0085] In one embodiment of this specification, L1 is a direct bond.

[0086] In one embodiment of this specification, L2 is a direct bond.

[0087] In one embodiment of this specification, one of L1 and L2 is directly bonded.

[0088] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each may be directly bonded or selected from any of the following structures.

[0089]

[0090] In the above structure, D refers to deuterium, k1 is an integer from 0 to 4, and k2 is an integer from 0 to 6.

[0091] In one embodiment of this specification, k1 is 1 or more. In another embodiment, k1 is 2 or more. In another embodiment, k1 is 3 or more. In another embodiment, k1 is 4.

[0092] In one embodiment of this specification, k2 is 1 or more. In another embodiment, k2 is 2 or more. In another embodiment, k2 is 3 or more. In another embodiment, k2 is 4 or more. In another embodiment, k2 is 5 or more. In another embodiment, k2 is 6.

[0093] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0094] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C2-C60 heterocyclic group.

[0095] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group.

[0096] In one embodiment of this specification, the heterocyclic groups of Ar1 and Ar2 contain O or S as heteroelements.

[0097] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted naphthobenzofuranyl, or a substituted or unsubstituted naphthobenzothiophenyl.

[0098] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently a C6-C30 aryl group substituted with or unsubstituted with deuterium; or a C2-C30 heterocyclic group substituted with or unsubstituted with deuterium, a C6-C30 aryl group, or a C6-C30 aryl group substituted with deuterium.

[0099] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, each being independently a C6-C20 aryl group substituted with or unsubstituted with deuterium; or a C2-C20 heterocyclic group substituted with or unsubstituted with deuterium, a C6-C20 aryl group, or a C6-C20 aryl group substituted with deuterium.

[0100] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently represents a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted terphenyl group; a deuterium-substituted or unsubstituted naphthyl group; a deuterium-substituted or unsubstituted phenanthryl group; a dibenzofuranyl group substituted or unsubstituted with deuterium, phenyl, or phenyl-d5 group; a dibenzothiophenyl group substituted or unsubstituted with deuterium, phenyl, or phenyl-d5 group; or a naphthobenzothiophenyl group substituted or unsubstituted with deuterium, phenyl, or phenyl-d5 group.

[0101] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each may independently be a deuterated or unsubstituted phenyl; a deuterated or unsubstituted 1-naphthyl; a deuterated or unsubstituted 2-naphthyl; a deuterated or unsubstituted 9-phenanthyl; a deuterated or unsubstituted 1-dibenzofuranyl; a deuterated, phenyl, or phenyl-d5yl; a deuterated, phenyl, or phenyl-d5yl; a deuterated, phenyl, or phenyl-d5yl; or a deuterated, phenyl, or phenyl-d5yl; or a deuterated, phenyl, or phenyl-d5yl; or a deuterated, phenyl, or phenyl-d5yl; or a deuterated, phenyl, or phenyl-d5yl; or a deuterated, phenyl, or phenyl-d5yl; or a deuterated, phenyl, or phenyl-d5yl;

[0102] In one embodiment of this specification, Ar1 is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted 1-naphthyl, or a deuterated or unsubstituted 2-naphthyl.

[0103] In one embodiment of this specification, Ar1 is a substituted or unsubstituted O-containing heterocyclic group or a substituted or unsubstituted S-containing heterocyclic group.

[0104] In one embodiment of this specification, Ar1 is an O-containing heterocyclic group of a tricyclic or tetracyclic ring substituted or unsubstituted with deuterium, aryl, or a deuterium-substituted aryl group; or an S-containing heterocyclic group of a tricyclic or tetracyclic ring substituted or unsubstituted with deuterium, aryl, or a deuterium-substituted aryl group.

[0105] In one embodiment of this specification, Ar1 is a dibenzofuranyl group substituted or unsubstituted with deuterium, phenyl or phenyl-d5 group; a dibenzothiophenyl group substituted or unsubstituted with deuterium, phenyl or phenyl-d5 group; a naphthobenzofuranyl group substituted or unsubstituted with deuterium, phenyl or phenyl-d5 group; or a naphthobenzothiophenyl group substituted or unsubstituted with deuterium, phenyl or phenyl-d5 group.

[0106] In one embodiment of this specification, Ar1 is 1-dibenzofuranyl substituted or unsubstituted with deuterium, phenyl or phenyl-d5 group; 2-dibenzofuranyl substituted or unsubstituted with deuterium, phenyl or phenyl-d5 group; 3-dibenzofuranyl substituted or unsubstituted with deuterium, phenyl or phenyl-d5 group; or 4-dibenzofuranyl substituted or unsubstituted with deuterium.

[0107] In one embodiment of this specification, Ar1 has the following chemical formula A1. When the Ar1 connected to anthracene has the following chemical formula A1, the high efficiency and long lifespan of the device are enhanced.

[0108] [Chemical Formula A1]

[0109]

[0110] In the above chemical formula A1,

[0111] Y1 is either O or S.

[0112] R1 to R8 may be the same as or different from each other, and each is independently a hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heterocyclic group, or may be combined with adjacent substituents to form a substituted or unsubstituted ring.

[0113] One of R1 to R8 is connected to L1 of the above chemical formula 1.

[0114] In one embodiment of this specification, Y1 is 0.

[0115] In one embodiment of this specification, Y1 is S.

[0116] In one embodiment of this specification, R1 to R8 may be the same as or different from each other, each being independently hydrogen, deuterium, or a C6-C30 aryl group substituted or unsubstituted with deuterium, or two adjacent substituents combined to form a benzene ring substituted or unsubstituted with deuterium.

[0117] In one embodiment of this specification, R1 to R8 may be the same or different from each other, each being independently hydrogen, deuterium, or a C6-C20 aryl group substituted or unsubstituted with deuterium, or two adjacent substituents combined to form a benzene ring substituted or unsubstituted with deuterium.

[0118] In one embodiment of this specification, R1 to R8 may be the same as or different from each other, each being independently hydrogen, deuterium, or a phenyl group substituted or unsubstituted with deuterium, or R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, or R7 and R8 may combine with each other to form a benzene ring substituted or unsubstituted with deuterium.

[0119] In one embodiment of this specification, the above chemical formula A1 is selected from one of the following structures.

[0120]

[0121] In the above structure,

[0122] Any one of a* to j* is connected to L1 of the above chemical formula 1.

[0123] D stands for deuterium.

[0124] k3 is an integer from 0 to 7, and k4 is an integer from 0 to 9.

[0125] The above structure is either substituted with or unsubstituted aryl groups, either by deuterium substitution or unsubstituted groups.

[0126] In one embodiment of this specification, the above structure is substituted or unsubstituted with aryl groups of C6-C20 that are either deuterated or unsubstituted.

[0127] In one embodiment of this specification, the above structure is substituted or unsubstituted with a phenyl group that is either deuterated or unsubstituted.

[0128] In one embodiment of this specification, a* is connected to L1 of the aforementioned chemical formula 1. In another embodiment, b* is connected to L1 of the aforementioned chemical formula 1. In another embodiment, c* is connected to L1 of the aforementioned chemical formula 1. In another embodiment, d* is connected to L1 of the aforementioned chemical formula 1. In another embodiment, e* is connected to L1 of the aforementioned chemical formula 1. In another embodiment, f* is connected to L1 of the aforementioned chemical formula 1. In another embodiment, g* is connected to L1 of the aforementioned chemical formula 1. In another embodiment, h* is connected to L1 of the aforementioned chemical formula 1. In another embodiment, i* is connected to L1 of the aforementioned chemical formula 1. In another embodiment, j* is connected to L1 of the aforementioned chemical formula 1.

[0129] In one embodiment of this specification, k3 is 1 or more. In another embodiment, k3 is 2 or more. In another embodiment, k3 is 3 or more. In another embodiment, k3 is 4 or more. In another embodiment, k3 is 5 or more. In another embodiment, k3 is 6 or more. In another embodiment, k3 is 7.

[0130] In one embodiment of this specification, k4 is 1 or more. In another embodiment, k4 is 2 or more. In another embodiment, k4 is 3 or more. In another embodiment, k4 is 4 or more. In another embodiment, k4 is 5 or more. In another embodiment, k4 is 6 or more. In another embodiment, k4 is 7 or more. In another embodiment, k4 is 8 or more. In another embodiment, k4 is 9.

[0131] In one embodiment of this specification, Ar2 is a C6-C30 aryl group that is either deuterated or unsubstituted.

[0132] In one embodiment of this specification, Ar2 is a C6-C20 aryl group that is either deuterated or unsubstituted.

[0133] In one embodiment of this specification, Ar2 is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted terphenyl, a deuterated or unsubstituted naphthyl, or a deuterated or unsubstituted phenanthryl.

[0134] In one embodiment of this specification, Ar2 is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted 1-naphthyl, a deuterated or unsubstituted 2-naphthyl, or a deuterated or unsubstituted 9-phenanthyl.

[0135] In one embodiment of this specification, Ar1 is the above-mentioned chemical formula A1, and L1 is direct bonding.

[0136] In one embodiment of this specification, Ar1 is the above-mentioned chemical formula A1, and Ar2 is a substituted or unsubstituted aryl group.

[0137] In one embodiment of this specification, Ar1 is the above-mentioned chemical formula A1, and Ar2 is a C6-C20 aryl group that is substituted with deuterium or not substituted.

[0138] In one embodiment of this specification, Ar1 is the above-mentioned chemical formula A1, and Ar2 is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted terphenyl, a deuterated or unsubstituted naphthyl, or a deuterated or unsubstituted phenanthryl.

[0139] In one embodiment of this specification, more than 50% of the aforementioned chemical formula 1 is deuterated. In another embodiment, more than 60% of the aforementioned chemical formula 1 is deuterated. In another embodiment, more than 70% of the aforementioned chemical formula 1 is deuterated. In another embodiment, more than 80% of the aforementioned chemical formula 1 is deuterated. In another embodiment, more than 90% of the aforementioned chemical formula 1 is deuterated. In another embodiment, 100% of the aforementioned chemical formula 1 is deuterated.

[0140] In one embodiment of this specification, the above-mentioned chemical formula 1 is selected from one of the following compounds.

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163] In another embodiment, the aforementioned chemical formula 1 is selected from one of the following compounds. Specifically, it is a compound of chemical formula 1 that includes the aforementioned chemical formula A1.

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193] The following is a detailed description of the compound with the following chemical formula 2.

[0194] [Chemical Formula 2]

[0195]

[0196] In one embodiment of this specification, D in chemical formula 2 is deuterium.

[0197] In one embodiment of this specification, n1 is an integer from 0 to 7.

[0198] In one embodiment of this specification, n1 is 0.

[0199] In one embodiment of this specification, L3 to L5 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0200] In one embodiment of this specification, L3 to L5 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C2-C60 divalent heterocyclic group.

[0201] In one embodiment of this specification, L3 to L5 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 divalent heterocyclic group.

[0202] In one embodiment of this specification, L3 to L5 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene.

[0203] In one embodiment of this specification, L3 to L5 may be the same as or different from each other, and each is independently directly bonded or phenylene.

[0204] In one embodiment of this specification, L3 is a direct bond.

[0205] In one embodiment of this specification, L4 is a direct bond.

[0206] In one embodiment of this specification, L5 is a direct bond.

[0207] In one embodiment of this specification, Ar3 and Ar4 may be the same as or different from each other, and each may be independently a cyano, a substituted or unsubstituted aryl, or a substituted or unsubstituted heterocyclic group.

[0208] In one embodiment of this specification, Ar3 and Ar4 may be the same as or different from each other, and each is independently a cyano group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C2-C60 heterocyclic group.

[0209] In one embodiment of this specification, Ar3 and Ar4 may be the same as or different from each other, and each is independently a cyano group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group.

[0210] In one embodiment of this specification, Ar3 and Ar4 may be the same as or different from each other, and each is independently a cyano group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group.

[0211] In one embodiment of this specification, Ar3 and Ar4 may be the same as or different from each other, each being independently a cyano group; a C6-C30 aryl group substituted or unsubstituted with a C1-C10 alkyl group or a C6-C30 aryl group; or a C2-C30 heterocyclic group substituted or unsubstituted with a C1-C10 alkyl group or a C6-C30 aryl group.

[0212] In one embodiment of this specification, Ar3 and Ar4 may be the same as or different from each other, and each is independently a cyano group; a C6-C20 aryl group substituted or unsubstituted with a C1-C6 alkyl group or a C6-C20 aryl group; or a C2-C20 heterocyclic group substituted or unsubstituted with a C1-C6 alkyl group or a C6-C20 aryl group.

[0213] In one embodiment of this specification, Ar3 and Ar4 may be the same as or different from each other, and each independently represents a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthyl group, a substituted or unsubstituted fluoranyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted triazine group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazine group, a substituted or unsubstituted benzimidazolyl group, or a substituted or unsubstituted group. At this point, Y3 and Y4 may be the same or different from each other, and each can be independently O, S or NR14.

[0214] In one embodiment of this specification, Ar3 and Ar4 may be the same as or different from each other, and each independently represents a cyano group, a phenyl group substituted or unsubstituted with methyl, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group substituted or unsubstituted with methyl or phenyl, a phenanthryl group, a fluoranyl group, a furanyl group, a thiophene group, a benzofuranyl group, a benzothiophene group, a dibenzofuranyl group, a dibenzothiophene group, a carbazoyl group substituted or unsubstituted with phenyl, a triazine group substituted or unsubstituted with methyl or phenyl, a pyrimidinyl group substituted or unsubstituted with methyl or phenyl, a pyridazine group substituted or unsubstituted with methyl or phenyl, a benzimidazolyl group substituted or unsubstituted with ethyl or phenyl, or... .

[0215] In one embodiment of this specification, Ar3 and Ar4 may be the same as or different from each other, and each independently represents phenyl, biphenyl, naphthyl, dimethylfluorenyl, diphenylfluorenyl, dibenzothiopheneyl or carbazoleyl.

[0216] In one embodiment of this specification, Ar3 may contain one or more cyano groups as substituents attached to Ar3, in addition to being the substituents described above.

[0217] In one embodiment of this specification, Ar4 may contain one or more cyano groups as substituents connected to Ar4, in addition to being the substituents described above.

[0218] In one embodiment of this specification, Ar5 is hydrogen, deuterium, cyano, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0219] In one embodiment of this specification, Ar5 is hydrogen, deuterium, cyano, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C2-C60 heterocyclic group.

[0220] In one embodiment of this specification, Ar5 is hydrogen, deuterium, cyano, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic group.

[0221] In one embodiment of this specification, Ar5 is hydrogen, deuterium, cyano, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C2-C20 heterocyclic group.

[0222] In one embodiment of this specification, Ar5 is hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl, substituted or unsubstituted triazineyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted benzimidazolyl, or substituted or unsubstituted. At this point, Y3 and Y4 may be the same or different from each other, and each can be O, S or N14 independently.

[0223] In one embodiment of this specification, Ar5 is hydrogen, deuterium, cyano, phenyl substituted or unsubstituted with methyl, biphenyl, terphenyl, naphthyl, fluorenyl substituted or unsubstituted with methyl or phenyl, phenanthyl, fluoranyl, furanyl, thienyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, carbazoyl substituted or unsubstituted with phenyl, triazineyl substituted or unsubstituted with methyl or phenyl, pyrimidinyl substituted or unsubstituted with methyl or phenyl, pyridinyl substituted or unsubstituted with methyl or phenyl, pyridazinyl substituted or unsubstituted with methyl or phenyl, benzimidazolyl substituted or unsubstituted with ethyl or phenyl, or... .

[0224] In one embodiment of this specification, Ar5 is hydrogen, phenyl, or dimethylfluorene.

[0225] In one embodiment of this specification, Ar5 may contain one or more cyano groups as substituents connected to Ar5, in addition to being the substituents described above.

[0226] In one embodiment of this specification, Ar3 and Ar4 may be the same as or different from each other, and each is independently selected from one of the following groups 1 or 2.

[0227] In one embodiment of this specification, Ar5 is hydrogen, deuterium, cyano, or selected from one of the following groups 1 or 2.

[0228] In one embodiment of this specification, Ar3 and Ar4 may be the same as or different from each other, each being independently selected from one of the following groups 1 or 2, and Ar5 is hydrogen, deuterium, cyano, selected from one of the following groups 1 or 2.

[0229] [Group 1]

[0230]

[0231] [Group 2]

[0232]

[0233] In groups 1 and 2 mentioned above,

[0234] The dashed line indicates the position where it connects to chemical formula 2 above.

[0235] Y3 is O, S, or NR14.

[0236] X1 to X5 may be the same as or different from each other, and each is independently N or CR15.

[0237] At least one of X1 to X5 is N.

[0238] R11 to R15 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0239] Cy1 is a monocyclic or polycyclic aromatic hydrocarbon ring, or a monocyclic or polycyclic aromatic heterocycle.

[0240] The structures of groups 1 and 2 above are substituted or unsubstituted by deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic groups.

[0241] In one embodiment of this specification, Y3 is NR14.

[0242] In one embodiment of this specification, Y3 is O or S.

[0243] In one embodiment of this specification, Cy1 is a benzene ring, a naphthyl ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring.

[0244] In one embodiment of this specification, Cy1 is a benzene ring, a naphthyl ring, or a dibenzofuran ring.

[0245] In one embodiment of this specification, R11 to R13 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl or a substituted or unsubstituted aryl.

[0246] In one embodiment of this specification, R11 to R13 may be the same as or different from each other, and each is independently a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C30 aryl group.

[0247] In one embodiment of this specification, R11 to R13 may be the same as or different from each other, and each is independently a substituted or unsubstituted methyl, a substituted or unsubstituted ethyl, or a substituted or unsubstituted phenyl.

[0248] In one embodiment of this specification, R11 and R12 are methyl groups.

[0249] In one embodiment of this specification, R13 is ethyl or phenyl.

[0250] In one embodiment of this specification, R14 is a substituted or unsubstituted aryl group.

[0251] In one embodiment of this specification, R14 is a substituted or unsubstituted aryl group of C6-C30.

[0252] In one embodiment of this specification, R14 is a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.

[0253] In one embodiment of this specification, R14 is a phenyl group.

[0254] In one embodiment of this specification, R15 is hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0255] In one embodiment of this specification, R15 is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C30 aryl group.

[0256] In one embodiment of this specification, R15 is hydrogen, deuterium, substituted or unsubstituted methyl, or substituted or unsubstituted phenyl.

[0257] In one embodiment of this specification, one or more of the plurality of R15 are substituted or unsubstituted alkyl groups or substituted or unsubstituted aryl groups.

[0258] In one embodiment of this specification, R15 is hydrogen, deuterium, methyl or phenyl, and one or more of R15 are methyl or phenyl.

[0259] In one embodiment of this specification, the structure of the above-mentioned group 2 is selected from one of the following groups 2-1.

[0260] [Group 2-1]

[0261]

[0262] In the above group 2-1,

[0263] The dashed line indicates the position where it connects to chemical formula 2 above.

[0264] Y3 and Y4 may be the same as or different from each other, and each is independently O, S, or NR14.

[0265] R13, R14, and R16 through R18 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0266] r16 is an integer from 0 to 3, and r16' is an integer from 0 to 4.

[0267] When r16 and r16' are each 2 or more, R16 can be the same or different from each other.

[0268] In one embodiment of this specification, Y3 is NR14.

[0269] In one embodiment of this specification, Y3 and Y4 may be the same as or different from each other, and each may be O or S independently.

[0270] In one embodiment of this specification, R16 to R18 may be described in the above description regarding R15.

[0271] In one embodiment of this specification, R16 to R18 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl or a substituted or unsubstituted aryl.

[0272] In one embodiment of this specification, R16 to R18 may be the same as or different from each other, and each is independently a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C30 aryl group.

[0273] In one embodiment of this specification, R16 to R18 may be the same as or different from each other, and each is independently a substituted or unsubstituted methyl or a substituted or unsubstituted phenyl.

[0274] In one embodiment of this specification, R16 is methyl or phenyl.

[0275] In one embodiment of this specification, r16 is 1 or more.

[0276] In one embodiment of this specification, r16 is 1.

[0277] In one embodiment of this specification, r16' is 1 or more.

[0278] In one embodiment of this specification, r16' is 2.

[0279] In one embodiment of this specification, R17 and R18 are phenyl groups.

[0280] In one embodiment of this specification, at least one of Ar3 and Ar4 is selected from one of the above-described groups 1.

[0281] In one embodiment of this specification, Ar3 is selected from one of the above-described groups 1.

[0282] In one embodiment of this specification, Ar4 is selected from one of the above-described groups 1.

[0283] In one embodiment of this specification, at least one of Ar3 to Ar5 is a cyano group, or contains one or more cyano groups as substituents. In this case, it means that at least one of Ar3 to Ar5 is 1) a cyano group, or 2) an aryl or heterocyclic group and contains one or more cyano groups as substituents of the aforementioned aryl or heterocyclic group.

[0284] In this specification, even if the above definitions of Ar3 to Ar5 do not explicitly state that the substituents are replaced by cyano groups, they may include the cases where the substituents are replaced by cyano groups.

[0285] In one embodiment of this specification, at least one of Ar3 to Ar5 is a cyano group, or the following chemical formula 201.

[0286] [Chemical Formula 201]

[0287]

[0288] In the above chemical formula 201,

[0289] Ar6 is a substituted or unsubstituted divalent to tetravalent aryl group, or a substituted or unsubstituted divalent to tetravalent heterocyclic group.

[0290] m1 is an integer from 1 to 3.

[0291] The dashed line connects to the above chemical formula 2.

[0292] In one embodiment of this specification, m1 is 1 or 2.

[0293] In one embodiment of this specification, m1 is 1.

[0294] In one embodiment of this specification, Ar6 is a substituted or unsubstituted divalent or tetravalent C6-C30 aryl group, or a substituted or unsubstituted divalent to tetravalent C2-C30 heterocyclic group.

[0295] In one embodiment of this specification, Ar6 is a substituted or unsubstituted divalent to tetravalent C6-C20 aryl group, or a substituted or unsubstituted divalent to tetravalent C2-C20 heterocyclic group.

[0296] In one embodiment of this specification, Ar6 is a substituted or unsubstituted divalent to tetravalent phenyl, a substituted or unsubstituted divalent to tetravalent biphenyl, a substituted or unsubstituted divalent to tetravalent terphenyl, a substituted or unsubstituted divalent to tetravalent naphthyl, a substituted or unsubstituted divalent to tetravalent fluorenyl, a substituted or unsubstituted divalent to tetravalent phenanthryl, a substituted or unsubstituted divalent to tetravalent fluoranyl, a substituted or unsubstituted divalent to tetravalent furanyl, a substituted or unsubstituted divalent to tetravalent thiophene, or a substituted or unsubstituted divalent to tetravalent benzo[a]]. Furanyl, substituted or unsubstituted divalent to tetravalent benzothiophene, substituted or unsubstituted divalent to tetravalent dibenzofuranyl, substituted or unsubstituted divalent to tetravalent dibenzothiophene, substituted or unsubstituted divalent to tetravalent carbazole, substituted or unsubstituted divalent to tetravalent triazine, substituted or unsubstituted divalent to tetravalent pyrimidinyl, substituted or unsubstituted divalent to tetravalent pyridinyl, substituted or unsubstituted divalent to tetravalent pyridazine, substituted or unsubstituted divalent to tetravalent benzimidazolyl, or substituted or unsubstituted divalent to tetravalent At this point, Y3 and Y4 may be the same or different from each other, and each can be O, S or N14 independently.

[0297] In one embodiment of this specification, Ar6 may be a structure based on a divalent or trivalent group selected from one of the groups 1 or 2 described above.

[0298] In one embodiment of this specification, Ar6 is a substituted or unsubstituted divalent to trivalent phenyl, a substituted or unsubstituted divalent to trivalent biphenyl, a substituted or unsubstituted divalent to trivalent terphenyl, a substituted or unsubstituted divalent to trivalent naphthyl, a substituted or unsubstituted divalent to trivalent fluorenyl, a substituted or unsubstituted divalent to trivalent furanyl, a substituted or unsubstituted divalent to trivalent thiophene, a substituted or unsubstituted divalent to trivalent benzofuranyl, a substituted or unsubstituted divalent to trivalent benzothiophene, a substituted or unsubstituted divalent to trivalent dibenzofuranyl, or a substituted or unsubstituted divalent to trivalent dibenzothiophene.

[0299] In one embodiment of this specification, Ar6 is a divalent to trivalent phenyl, a divalent to trivalent biphenyl, a divalent to trivalent terphenyl, a divalent to trivalent naphthyl, a divalent to trivalent fluorenyl substituted with or unsubstituted with methyl or phenyl, a divalent to trivalent furanyl, a divalent to trivalent thiophene, a divalent to trivalent benzofuranyl, a divalent to trivalent benzothiophene, a divalent to trivalent dibenzofuranyl, or a divalent to trivalent dibenzothiophene.

[0300] In one embodiment of this specification, Ar6 is a substituted or unsubstituted divalent to tetravalent C6-C30 aryl group.

[0301] In one embodiment of this specification, Ar6 is a substituted or unsubstituted divalent to trivalent C6-C20 aryl group.

[0302] In one embodiment of this specification, Ar6 is a divalent to trivalent phenyl, a divalent to trivalent biphenyl, a divalent to trivalent terphenyl, a divalent to trivalent naphthyl, or a divalent to trivalent fluorenyl substituted with or unsubstituted with methyl or phenyl.

[0303] In one embodiment of this specification, at least one of Ar3 to Ar5 is a cyano group, or any one of the following chemical formulas 202 to 204.

[0304] [Chemical formula 202]

[0305]

[0306] [Chemical formula 203]

[0307]

[0308] [Chemical Formula 204]

[0309]

[0310] In the above chemical formulas 202 to 204,

[0311] m1 is an integer from 1 to 3.

[0312] Ar61 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0313] R21 is hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0314] R22 and R23 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0315] r21 is an integer from 0 to 4, and r21' and r21'' are each integers from 0 to 6.

[0316] When r21, r21', and r21'' are each 2 or more, R21 may be the same or different from each other.

[0317] The dashed line connects to the above chemical formula 2.

[0318] In one embodiment of this specification, R21 is hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0319] In one embodiment of this specification, R21 is hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic group.

[0320] In one embodiment of this specification, R21 is hydrogen, deuterium, cyano, or a substituted or unsubstituted phenyl group.

[0321] In one embodiment of this specification, R21 is hydrogen or phenyl.

[0322] In one embodiment of this specification, R22 and R23 may be the same as or different from each other, and each is independently a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C30 aryl group.

[0323] In one embodiment of this specification, R22 and R23 may be the same as or different from each other, and each may be independently a substituted or unsubstituted methyl or a substituted or unsubstituted phenyl.

[0324] In one embodiment of this specification, R22 and R23 may be the same as or different from each other, and each may be independently methyl or phenyl.

[0325] In one embodiment of this specification, the above description of Ar6 is applied to Ar61.

[0326] In one embodiment of this specification, Ar61 is a directly bonded, substituted, or unsubstituted C6-C30 aryl group.

[0327] In one embodiment of this specification, Ar61 is a directly bonded, substituted, or unsubstituted C6-C20 aryl group.

[0328] In one embodiment of this specification, Ar61 is a directly bonded, substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenylene.

[0329] In one embodiment of this specification, Ar61 is directly bonded or phenylene.

[0330] In one embodiment of this specification, r21 is 1.

[0331] In one embodiment of this specification, r21' and r21'' are 0.

[0332] In one embodiment of this specification, the above chemical formula 202 is represented by any one of the following chemical formulas 202-1 to 202-5.

[0333] [Chemical Formula 202-1]

[0334]

[0335] [Chemical Formula 202-2]

[0336]

[0337] [Chemical Formula 202-3]

[0338]

[0339] [Chemical Formula 202-4]

[0340]

[0341] [Chemical Formula 202-5]

[0342]

[0343] In the above chemical formulas 202-1 to 202-5,

[0344] Ar61, R21, r21, and the dashed line are the same as those defined in the above chemical formula 202.

[0345] r211 is an integer from 0 to 3. When r211 is 2 or higher, R21 is either the same or different from each other.

[0346] In one embodiment of this specification, the above chemical formula 202 is any one of the above chemical formulas 202-2 to 202-5.

[0347] In one embodiment of this specification, the above chemical formula 202 is the above chemical formula 202-2 or 202-3.

[0348] In one embodiment of this specification, Ar3 is a cyano group, or contains one or more cyano groups as substituents. In another embodiment, Ar3 is a cyano group, or any one of the above chemical formulas 202 to 204.

[0349] In one embodiment of this specification, Ar4 is a cyano group, or contains one or more cyano groups as substituents. In another embodiment, Ar4 is a cyano group, or any one of the above chemical formulas 202 to 204.

[0350] In one embodiment of this specification, Ar5 is a cyano group, or contains one or more cyano groups as substituents. In another embodiment, Ar5 is a cyano group, or any one of the above chemical formulas 202 to 204.

[0351] In one embodiment of this specification, the above-mentioned chemical formula 2 is selected from one of the following compounds.

[0352]

[0353]

[0354]

[0355]

[0356]

[0357] The compound according to one embodiment of this specification can be manufactured by the manufacturing method described later. Substituents can be added or removed as needed, and the positions of the substituents can be changed. Furthermore, based on techniques known in the art, the starting material, reactants, reaction conditions, etc., can be changed. The manufacturing method can be further specified in the manufacturing examples described later, and the reaction sequence can be changed depending on the compound. The synthesis method of the compounds of chemical formulas 1 and 2 is not limited to the methods described above.

[0358] This specification provides organic light-emitting devices containing the compounds described above.

[0359] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0360] In this specification, when a part is indicated to "include / comprise" a certain element, unless otherwise stated, it means that other elements may be included, rather than excluding other elements.

[0361] In this specification, the term "layer" is used interchangeably with "film" primarily used in this technical field, referring to a coating covering a target area. The size of the "layer" is not limited; the sizes of individual "layers" can be the same or different. In one embodiment, the size of a "layer" can be equal to the size of the entire device, equivalent to the size of a specific functional area, or as small as a single sub-pixel.

[0362] In this specification, the inclusion of a specific substance A in layer B means including both i) the case where one or more substances A are included in a single layer of layer B, and ii) the case where layer B consists of one or more layers and substances A are included in one or more layers of multiple layers of layer B.

[0363] In this specification, the inclusion of a specific substance A in layer C or layer D means that i) it is included in more than one layer of layer C, or ii) it is included in more than one layer of layer D, or iii) it is included in both more than one layer of layer C and more than one layer of layer D.

[0364] The organic layer of the organic light-emitting device described in this specification can be formed as a single-layer structure or as a multi-layer structure with two or more organic layers stacked on top of each other. For example, it can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. However, the structure of the organic light-emitting device is not limited to this.

[0365] The organic light-emitting device described in this specification contains a compound of formula 1 in the light-emitting layer and a compound of formula 2 in the first organic layer.

[0366] In one embodiment of this specification, the first organic layer is disposed between the light-emitting layer and the cathode. That is, the first organic layer is included in the electron transport region.

[0367] In one embodiment of this specification, the first organic layer is configured to be in direct contact with the light-emitting layer. In this case, no additional organic layer is present between the light-emitting layer and the first organic layer.

[0368] In one embodiment of this specification, the first organic layer is disposed between the light-emitting layer and the cathode, and is configured to be in direct contact with the light-emitting layer.

[0369] In one embodiment of this specification, the first organic layer is configured to be directly in contact with the cathode. In this case, no additional organic layer is present between the cathode and the first organic layer.

[0370] In one embodiment of this specification, the light-emitting layer comprises a host and a dopant. In one embodiment, the host comprises a compound of chemical formula 1.

[0371] In one embodiment of this specification, the dopant includes a phosphorescent dopant or a fluorescent dopant. As a fluorescent dopant, it may comprise an arylamine compound or a boron compound.

[0372] In one embodiment of this specification, the dopant is an arylamine compound containing a pyrene group. Specifically, it is a compound with the following chemical formula Z1.

[0373] [Chemical Formula Z1]

[0374]

[0375] In the above chemical formula Z1,

[0376] Ar31 to Ar34 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0377] R31 and R32 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0378] r31 and r32 are integers from 0 to 4. When they are 2 or higher, the substituents in the parentheses are either the same or different from each other.

[0379] In one embodiment of this specification, Ar31 to Ar34 are aryl groups substituted with or unsubstituted with deuterium, alkyl or cyano groups.

[0380] In one embodiment of this specification, R31 and R32 are hydrogen, deuterium, or substituted or unsubstituted alkylsilyl groups.

[0381] In one embodiment of this specification, the above chemical formula Z1 contains a cyano or silyl group. At least one of R31, R32, Ar31 and Ar34 is a cyano or silyl group, or contains a cyano or silyl group as a substituent.

[0382] In one embodiment of this specification, the above-mentioned chemical formula Z1 is the following compound.

[0383]

[0384] In one embodiment of this specification, the light-emitting layer may contain 0.01 to 50 parts by weight of dopant, preferably 0.1 to 30 parts by weight, and more preferably 1 to 10 parts by weight, based on 100 parts by weight of the main body. Within the above ranges, energy transfer from the main body to the dopant is effectively generated.

[0385] In one embodiment of this specification, the organic layer includes two or more light-emitting layers, one of which contains a compound of chemical formula 1.

[0386] In one embodiment of this specification, the maximum emission peaks of the two or more light-emitting layers are different from each other. The light-emitting layer containing the compound of Formula 1 is blue, and the light-emitting layer not containing the compound of Formula 1 may contain blue, red, or green light-emitting compounds known in the art.

[0387] In one embodiment of this specification, the light-emitting layer containing the compound of Formula 1 contains a fluorescent dopant, and the light-emitting layer not containing the compound of Formula 1 contains a phosphorescent dopant.

[0388] In one embodiment of this specification, the maximum emission peak of the luminescent layer containing the compound of Formula 1 is located in the range of 400 nm to 500 nm. That is, the luminescent layer containing the compound of Formula 1 emits blue light.

[0389] According to one embodiment of this specification, the organic layer of the organic light-emitting device includes two or more light-emitting layers. The maximum emission peak of one light-emitting layer (light-emitting layer 1) is located in the range of 400 nm to 500 nm, and the maximum emission peak of another light-emitting layer (light-emitting layer 2) is located in the range of 510 nm to 580 nm or 610 nm to 680 nm. In this case, light-emitting layer 1 contains a compound of the aforementioned chemical formula 1.

[0390] In one embodiment of this specification, the first organic layer is an electron transport region. Specifically, it is an electron injection layer, an electron transport layer, an electron injection and transport layer, or a hole blocking layer.

[0391] In one embodiment of this specification, the first organic layer further comprises one or more n-type dopants selected from alkali metals and alkaline earth metals.

[0392] When organoalkali metal compounds or organoalkaline earth metal compounds are used as n-type dopants, the stability of holes in the emissive layer can be ensured, thereby improving the lifetime of organic light-emitting devices. Furthermore, the electron mobility of the electron transport layer and the proportion of organoalkali metal compounds or organoalkaline earth metal compounds can be adjusted to maximize the balance between holes and electrons in the emissive layer, thereby increasing luminous efficiency.

[0393] In this specification, LiQ is more preferably used as a dopant for the first n-type organic layer.

[0394] The first organic layer may contain the compound of chemical formula 2 and the aforementioned n-type dopant in a weight ratio of 1:9 to 9:1. Preferably, it may contain the compound of chemical formula 2 and the aforementioned n-type dopant in a weight ratio of 2:8 to 8:2, and more preferably, it may contain them in a weight ratio of 3:7 to 7:3.

[0395] In one embodiment of this specification, the first organic layer is configured to be in direct contact with the light-emitting layer and contains the compound of chemical formula 2 and an n-type dopant.

[0396] In one embodiment of this specification, the first organic layer is configured to be directly connected to the cathode and contains the compound of formula 2. In this case, the first organic layer does not contain any compounds other than the compound of formula 2. Furthermore, other organic layers (specifically, hole-blocking layers) may be present between the first organic layer and the light-emitting layer.

[0397] In one embodiment of this specification, the organic layer of the organic light-emitting device has a hole transport region between the anode and the light-emitting layer. In this case, the hole transport region includes one or more of the following: a hole injection layer, a hole injection layer, a hole injection and transport layer, and an electron blocking layer.

[0398] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0399] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0400] The organic light-emitting device structure described in this specification can have the following characteristics: Figure 1 , Figure 2 and Figure 8 The structure shown is not limited to this.

[0401] exist Figure 1The diagram illustrates the structure of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 11. In the structure described above, the compound of chemical formula 1 may be included in the light-emitting layer 6, and the compound of chemical formula 2 may be included in the hole blocking layer 7 or the electron injection and transport layer 8.

[0402] exist Figure 2 The diagram illustrates the structure of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, an electron injection and transport layer 8, and a cathode 11. In the structure described above, the compound of chemical formula 1 may be included in the light-emitting layer 6, and the compound of chemical formula 2 may be included in the electron injection and transport layer 8.

[0403] Figure 8 The diagram illustrates the structure of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a p-doped hole transport layer 4p, a red hole transport layer 4R, a green hole transport layer 4G, a blue hole transport layer 4B, a red phosphorescent layer 6RP, a green phosphorescent layer 6GP, a blue fluorescent layer 6BF, a first electron transport layer 9a, a second electron transport layer 9b, an electron injection layer 10, a cathode 11, and a capping layer 14. In the structure described above, the compound of Chemical Formula 1 may be included in the red phosphorescent layer 6RP, the green phosphorescent layer 6GP, and the blue fluorescent layer 6BF, and the compound of Chemical Formula 2 may be included in one or more of the first electron transport layer 9a, the second electron transport layer 9b, and the electron injection layer 10.

[0404] According to one embodiment of this specification, the organic light-emitting device can be a series structure of two or more independent devices connected in series. In one embodiment, the series structure can be a configuration in which the individual organic light-emitting devices are bonded together by a charge-generating layer. Based on the same brightness, the devices in the series structure can be driven at lower currents compared to a single device, thus offering the advantage of significantly improved device lifetime characteristics.

[0405] According to one embodiment of the basic specification, the organic layer includes: a first stack comprising one or more light-emitting layers; a second stack comprising one or more light-emitting layers; and a charge-generating layer disposed between the first stack and the second stack.

[0406] According to one embodiment of this specification, the organic layer includes: a first stack comprising one or more light-emitting layers; a second stack comprising one or more light-emitting layers; and a third stack comprising one or more light-emitting layers, wherein one or more charge-generating layers are each included between the first stack and the second stack, and between the second stack and the third stack.

[0407] In this specification, the charge generating layer refers to the layer that generates holes and electrons when a voltage is applied. This charge generating layer can be an N-type charge generating layer or a P-type charge generating layer. In this specification, an N-type charge generating layer refers to a charge generating layer positioned closer to the anode than a P-type charge generating layer, and a P-type charge generating layer refers to a charge generating layer positioned closer to the cathode than an N-type charge generating layer.

[0408] The aforementioned N-type charge generation layer and P-type charge generation layer can be connected together to form an NP junction. Through the NP junction, holes easily form in the P-type charge generation layer, and electrons easily form in the N-type charge generation layer. Electrons are transported towards the anode via the LUMO energy level of the N-type charge generation layer, while holes are transported towards the cathode via the HOMO energy level of the P-type organic layer.

[0409] The first stack, the second stack, and the third stack each include one or more light-emitting layers, and may further include one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a layer that simultaneously performs hole transport and hole injection (hole injection and transport layer), and a layer that simultaneously performs electron transport and electron injection (electron injection and transport layer).

[0410] An organic light-emitting device including the first stack and the second stack described above is exemplified in... Figure 3 .

[0411] exist Figure 3 The diagram illustrates the structure of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light-emitting layer 6a, a first electron transport layer 9a, an N-type charge generation layer 12, a P-type charge generation layer 13, a second hole transport layer 4b, a second light-emitting layer 6b, an electron injection and transport layer 8, and a cathode 11. In the structure described above, the compound of chemical formula 1 may be included in the first light-emitting layer 6a or the second light-emitting layer 6b, and the compound of chemical formula 2 may be included in the first electron transport layer 9a or the electron injection and transport layer 8.

[0412] An organic light-emitting device including the first to third stacks described above is exemplified in... Figures 4 to 7 .

[0413] exist Figure 4 The diagram illustrates the structure of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light-emitting layer 6a, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a second hole transport layer 4b, a second light-emitting layer 6b, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a third hole transport layer 4c, a third light-emitting layer 6c, a third electron transport layer 9c, and a cathode 11. In the structure described above, the compound of Chemical Formula 1 may be included in the first light-emitting layer 6a, the second light-emitting layer 6b, and the third light-emitting layer 6c, and the compound of Chemical Formula 2 may be included in one or more of the first electron transport layer 9a, the second electron transport layer 9b, and the third electron transport layer 9c.

[0414] exist Figure 5 The diagram illustrates the structure of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light-emitting layer 6BFa, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a third hole transport layer 4c, a red phosphorescent light-emitting layer 6RP, a yellow-green phosphorescent light-emitting layer 6YGP, a green phosphorescent light-emitting layer 6GP, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a fourth hole transport layer 4d, a fifth hole transport layer 4e, a second blue fluorescent light-emitting layer 6BFb, a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a capping layer 14. In the structure described above, the compound of chemical formula 1 may be contained in the first blue fluorescent emitting layer 6BFa or the second blue fluorescent emitting layer 6BFb, and the compound of chemical formula 2 may be contained in one or more of the first electron transport layer 9a, the second electron transport layer 9b, the third electron transport layer 9c and the electron injection layer 10.

[0415] exist Figure 6The diagram illustrates the structure of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light-emitting layer 6BFa, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a third hole transport layer 4c, a red phosphorescent light-emitting layer 6RP, a green phosphorescent light-emitting layer 6GP, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a fourth hole transport layer 4d, a fifth hole transport layer 4e, a second blue fluorescent light-emitting layer 6BFb, a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a capping layer 14. In the structure described above, the compound of chemical formula 1 may be contained in the first blue fluorescent emitting layer 6BFa or the second blue fluorescent emitting layer 6BFb, and the compound of chemical formula 2 may be contained in one or more of the first electron transport layer 9a, the second electron transport layer 9b, the third electron transport layer 9c and the electron injection layer 10.

[0416] exist Figure 7 The diagram illustrates the structure of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a first p-doped hole transport layer 4pa, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light-emitting layer 6BFa, a first electron transport layer 9a, a first N-type charge generation layer 12a, a first P-type charge generation layer 13a, a third hole transport layer 4c, a fourth hole transport layer 4d, a second blue fluorescent light-emitting layer 6BFb, a second electron transport layer 9b, a second N-type charge generation layer 12b, a second P-type charge generation layer 13b, a fifth hole transport layer 4e, a sixth hole transport layer 4f, a third blue fluorescent light-emitting layer 6BFc, a third electron transport layer 9c, an electron injection layer 10, a cathode 11, and a capping layer 14. In the structure described above, the compound of chemical formula 1 may be contained in one or more of the first blue fluorescent emitting layer 6BFa, the second blue fluorescent emitting layer 6BFb, and the third blue fluorescent emitting layer 6BFc, and the compound of chemical formula 2 may be contained in one or more of the first electron transport layer 9a, the second electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10.

[0417] The aforementioned N-type charge-generating layer can be 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanodimethyl-p-benzoquinone (F4TCNQ), fluorine-substituted 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylamine derivatives, etc., but is not limited to these. In one embodiment, the aforementioned N-type charge-generating layer may simultaneously contain benzimidazole-phenanthrene derivatives and Li metal.

[0418] The aforementioned P-type charge-generating layer can simultaneously contain aryl amine derivatives and compounds containing cyano groups.

[0419] The organic light-emitting devices described in this specification, except that the organic layer contains the aforementioned compounds, can be manufactured using materials and methods known in the art.

[0420] When the aforementioned organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0421] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; then forming an organic layer on the anode, comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer; and finally depositing a material suitable for use as a cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0422] In addition to vacuum evaporation, solution coating can also be used to form organic layers from compounds when manufacturing organic light-emitting devices. Here, solution coating refers to methods such as spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roll coating, but is not limited to these.

[0423] In addition to these methods, organic light-emitting devices can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. However, the manufacturing method is not limited to these methods.

[0424] As the aforementioned anode material, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. Examples include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but these are not limited to these.

[0425] As the cathode material mentioned above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer materials such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0426] The aforementioned luminescent layer may comprise a host material and a dopant material. The host material may be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but are not limited to these.

[0427] As dopant materials, there are aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, benzo[a]pyrene, and diind[b]pyrene. Furthermore, styrene amine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrene amines, styrene diamines, styrene triamines, and styrene tetraamines, but these are not limited to these. Furthermore, as metal complexes, there are iridium complexes and platinum complexes, but these are not limited to these.

[0428] The aforementioned hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, the effect of receiving holes from the anode, and an excellent hole injection effect on the light-emitting layer or light-emitting material. Furthermore, it is preferably a material with excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material. Moreover, it is preferably a material with excellent thin film forming ability. Furthermore, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds; hexanitrile hexaazabenzophenanthrene-based organic compounds; quinacridone-based organic compounds; perylene-based organic compounds; anthraquinones, polyaniline, and polythiophene-based conductive polymers.

[0429] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. It can be a single layer or a multilayer structure with two or more layers. The hole transport material is a material capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer, and is preferably a material with a high hole mobility. Specific examples include arylamine-based organic compounds, carbazole-based compounds, conductive polymers, and block copolymers that simultaneously contain conjugated and non-conjugated portions, but are not limited to these.

[0430] In one embodiment of this specification, the hole transport layer is a multilayer structure with two or more layers. Specifically, it is a two-layer structure, and each layer contains different substances.

[0431] The aforementioned electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, preferably a material with high electron mobility. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, and hydroxyflavonoid-metal complexes, but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, suitable cathode materials are typically materials with low work functions and accompanied by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, all of which are accompanied by an aluminum or silver layer.

[0432] The aforementioned electron injection layer is a layer that receives electrons from the electrode. The preferred electron injection material is one that exhibits excellent electron transport capabilities, effectively receives electrons from the second electrode, and provides excellent electron injection for the light-emitting layer or light-emitting material. Furthermore, it is preferably a material that prevents excitons generated in the light-emitting layer from migrating to the hole injection layer and possesses excellent thin-film formation capabilities. Specifically, materials such as fluorenone, anthraquinone dimethyl ether, biphenylquinone, and thiamethoxam dioxide are preferred. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0433] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0434] The aforementioned electron blocking layer prevents electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer, thereby improving the device's lifetime and efficiency. It can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport, without limitation using known materials.

[0435] The aforementioned hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed using the same conditions as the electron injection layer. Specifically, there are... Diazole or triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, etc., but not limited to these.

[0436] Depending on the materials used, the organic light-emitting device according to this specification can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0437] The organic light-emitting devices according to this specification can be included in and used in various electronic devices. For example, the aforementioned electronic devices can be display panels, touch panels, solar modules, lighting devices, etc., but are not limited thereto.

[0438] Implementation of the invention

[0439] Hereinafter, in order to provide a detailed description of this specification, embodiments and comparative examples will be given. However, various modifications can be made based on the embodiments and comparative examples described herein, and this should not be construed as limiting the scope of this specification to the embodiments and comparative examples detailed below. The embodiments and comparative examples in this specification are provided to provide a more complete explanation of this specification to those skilled in the art.

[0440] Manufacturing Example 1-1: Manufacturing of Compound B1

[0441]

[0442] Compound B1-P0 (26.5 g, 87.1 mmol) and AlCl3 (0.5 g) were added to C6D6 (400 ml) and stirred for 2 hours. After the reaction was complete, D2O (60 ml) was added, and the mixture was stirred for 30 minutes. Then, trimethylamine (6 ml) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over anhydrous magnesium sulfate (MgSO4) and recrystallized from ethyl acetate to give compound B1-P1 (19.3 g, 69%).

[0443] MS:[M+H] + =321

[0444] Compound B1-P1 (19.0 g, 59.3 mmol), N-bromosuccinimide (NBS) (11.6 g, 65.2 mmol), and 300 mL of dimethylformamide (DMF) were added. The mixture was stirred at room temperature under an argon atmosphere for 8 hours. After the reaction was complete, the organic layer was extracted with water and ethyl acetate. The extract was dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated under reduced pressure, and the sample was purified by silica gel column chromatography to obtain compound B1-P2 (17.0 g, 72%).

[0445] MS:[M+H] + =398

[0446] Under a nitrogen atmosphere, B1-P2 (15 g, 37.7 mmol) and naphth-1-ylboronic acid (6.5 g, 37.7 mmol) were added to 300 ml of 1,4-di(2 ... In an alkane, the mixture was stirred and refluxed. Then, potassium carbonate (15.6 g, 113 mmol) was dissolved in 16 mL of water and added to the mixture. After thorough stirring, tetrakis(triphenyl)phosphine-palladium (1.3 g, 1.1 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in 20 times its volume (336 mL) of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound B1 (9.9 g, 59%, MS: [M+H]). + =446.6).

[0447] Manufacturing Examples 1-2: Manufacturing of Compound B2

[0448]

[0449] The above-described compound B2 was manufactured using the starting materials as shown in the reaction formula above, except that the same method as that used in Manufacturing Example 1-1 above was employed.

[0450] MS:[M+H] + =526

[0451] Manufacturing Examples 1-3: Manufacturing of Compound B3

[0452]

[0453] The above-described compound B3 was manufactured using the starting materials as shown in the reaction formula above, except that the same method as that used in Manufacturing Example 1-1 above was employed.

[0454] MS:[M+H] + =486

[0455] Manufacturing Examples 1-4: Manufacturing of Compound B4

[0456]

[0457] The above-described compound B4 was manufactured using the starting materials as shown in the reaction formula above, except that the same method as that used in Manufacturing Example 1-1 above was employed.

[0458] MS:[M+H] + =484

[0459] Manufacturing Examples 1-5: Manufacturing of Compound B5

[0460]

[0461] The above-described compound B5 was manufactured using the starting materials as shown in the reaction formula above, except that the same method as that used in Manufacturing Example 1-1 above was employed.

[0462] MS:[M+H] + =592

[0463] Manufacturing Examples 1-6: Manufacturing of Compound B6

[0464]

[0465] The above-described compound B6 was produced using the starting materials as shown in the reaction formula above, except that the same method was used to produce B1-P1 as in the above-described manufacturing example 1-1.

[0466] MS:[M+H] + =453

[0467] Manufacturing Examples 1-7: Manufacturing of Compound B7

[0468]

[0469] The above-described compound B7 was produced using the starting materials as shown in the reaction formula above, except that the same method was used to produce B1-P1 as in Manufacturing Example 1-1 above.

[0470] MS:[M+H] + =533

[0471] Manufacturing Examples 1-8: Manufacturing of Compound B8

[0472]

[0473] The above-described compound B8 was produced using the starting materials as shown in the reaction formula above, except that the same method was used to produce B1-P1 as in the above-described manufacturing example 1-1.

[0474] MS:[M+H] + =493

[0475] Manufacturing Examples 1-9: Manufacturing of Compound B9

[0476]

[0477] The above-described compound B9 was produced using the starting materials as shown in the reaction formula above, except that the same method as that used to produce B1-P1 in Example 1-1 above was employed.

[0478] MS:[M+H] + =493

[0479] Manufacturing Examples 1-10: Manufacturing of Compound B10

[0480]

[0481] Using the starting materials as shown in the above reaction formula, the above compound B10 was manufactured by the same method as that used to manufacture compound B1-P1 in manufacturing example 1-1.

[0482] MS:[M+H] + =601

[0483] Manufacturing Example 2-1: Manufacturing of Compound E1

[0484]

[0485] Using the starting materials as shown in the above reaction formula, the above compound E1 was manufactured by the same method as that used to manufacture compound B1 in manufacturing example 1-1.

[0486] MS:[M+H] + =432

[0487] Manufacturing Example 2-2: Manufacturing of Compound E2

[0488]

[0489] Using the starting materials as shown in the above reaction formula, the above compound E2 was manufactured by the same method as that used to manufacture compound B1 in manufacturing example 1-1.

[0490] MS:[M+H] + =482

[0491] Manufacturing Example 2-3: Manufacturing of Compound E3

[0492]

[0493] Using the starting materials as shown in the above reaction formula, the above compound E3 was manufactured by the same method as that used to manufacture compound B1 in manufacturing example 1-1.

[0494] MS:[M+H] + =521

[0495] Manufacturing Example 2-4: Manufacturing of Compound E4

[0496]

[0497] Using the starting materials as shown in the above reaction formula, the above compound E4 was manufactured by the same method as that used to manufacture compound B1 in manufacturing example 1-1.

[0498] MS:[M+H] + =538

[0499] Manufacturing Example 2-5: Manufacturing of Compound E5

[0500]

[0501] Using the starting materials as shown in the above reaction formula, the above compound E5 was manufactured by the same method as that used to manufacture compound B1 in manufacturing example 1-1.

[0502] MS:[M+H] + =508

[0503] Manufacturing Example 2-6: Manufacturing of Compound E6

[0504]

[0505] Using the starting materials as shown in the above reaction formula, the above compound E6 was manufactured by the same method as that used to manufacture compound B1 in manufacturing example 1-1.

[0506] MS:[M+H] + =457

[0507] Manufacturing Example 2-7: Manufacturing of Compound E7

[0508]

[0509] Using the starting materials as shown in the above reaction formula, the above compound E7 was manufactured by the same method as that used to manufacture compound B1 in manufacturing example 1-1.

[0510] MS:[M+H] + =672

[0511] Manufacturing Example 2-8: Manufacturing of Compound E8

[0512]

[0513] Using the starting materials as shown in the above reaction formula, the above compound E8 was manufactured by the same method as that used to manufacture compound B1 in manufacturing example 1-1.

[0514] MS:[M+H] + =548

[0515] Example 1-1.

[0516] A glass substrate coated with an ITO (indium tin oxide) film at a thickness of 1000 Å was immersed in distilled water containing detergent and ultrasonically washed. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the ultrasonic washing was repeated twice with distilled water for 10 minutes each time. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0517] On the prepared ITO transparent electrode, the following HI-A compound is thermally vacuum-deposited to a thickness of 600 Å to form a hole injection layer.

[0518] On the aforementioned hole injection layer, the following HAT compound 50Å and the following compound HT-A 60Å are sequentially vacuum-deposited to form a first hole transport layer and a second hole transport layer.

[0519] Next, on the second hole transport layer, a light-emitting layer is formed by vacuum evaporation of compounds B1 and BD manufactured in Manufacturing Example 1-1 at a weight ratio of 25:1 with a film thickness of 200 Å.

[0520] On the light-emitting layer described above, compound E1 manufactured in manufacturing example 2-1 is vacuum-deposited to form an electron injection and transport layer with a thickness of 350 Å.

[0521] On the aforementioned electron injection and transport layer, lithium fluoride (LiF) is deposited sequentially with a thickness of 10 Å and aluminum with a thickness of 1000 Å to form a cathode.

[0522] During the above process, the evaporation rate of organic materials was maintained at 0.4 Å / s to 0.9 Å / s, the evaporation rate of lithium fluoride at the cathode was maintained at 0.3 Å / s, and the evaporation rate of aluminum was maintained at 2 Å / s. The vacuum level was maintained at 1 × 10⁻⁶ during evaporation. -7 Up to 5×10 -5 This led to the creation of organic light-emitting devices.

[0523]

[0524] Examples 1-2 to 1-80.

[0525] Organic light-emitting devices were manufactured using the compounds listed in Table 1 below instead of compounds B1 and E1 in Examples 1-1 above, except that organic light-emitting devices were manufactured by the same method as in Examples 1-1 above.

[0526]

[0527]

[0528] Comparative Examples 1-1 to 1-90.

[0529] Organic light-emitting devices were manufactured using the compounds listed in Table 1 below instead of compounds B1 and E1 in Examples 1-1 above, except that organic light-emitting devices were manufactured by the same method as in Examples 1-1 above.

[0530]

[0531]

[0532] For the organic light-emitting devices manufactured in Examples 1-1 to 1-80 and Comparative Examples 1-1 to 1-90 above, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time (T90) at the given current density was measured relative to the initial brightness, which was 90%. The results are shown in Table 1 below.

[0533] [Table 1]

[0534]

[0535]

[0536]

[0537]

[0538]

[0539]

[0540] Comparing Examples 1-1 to 1-80 in Table 1 above with Comparative Examples 1-1 to 1-16, it can be confirmed that the organic light-emitting devices using heterocyclic compounds of Formula 2 according to this specification (Examples 1-1 to 1-80) exhibit significantly superior characteristics in terms of voltage, efficiency, and lifetime compared to organic light-emitting devices using structures of Formula 2 without cyano groups in their framework (Comparative Examples 1-1 to 1-16).

[0541] Comparing Examples 1-1 to 1-80 in Table 1 above with Comparative Examples 1-17 to 1-48, it can be confirmed that the organic light-emitting devices (Examples 1-1 to 1-80) using compounds of Formula 1 according to this specification exhibit significantly superior lifetime characteristics compared to organic light-emitting devices (Comparative Examples 1-17 to 1-48) using structures with the same skeleton as Formula 1 but where deuterium is not linked to anthracene but to other substituents.

[0542] Comparing Examples 1-1 to 1-80 in Table 1 above with Comparative Examples 1-49 to 1-80, it can be confirmed that the organic light-emitting devices (Examples 1-1 to 1-80) using compounds of Formula 1 according to this specification exhibit significantly superior characteristics in terms of lifetime compared to organic light-emitting devices (Comparative Examples 1-49 to 1-80) using structures with the same skeleton as Formula 1 but without the substitution of deuterium.

[0543] Comparing Examples 1-1 to 1-80 in Table 1 above with Comparative Examples 1-81 to 1-90, it can be confirmed that the organic light-emitting devices using compounds of chemical formula 2 according to this specification (Examples 1-1 to 1-80) exhibit significantly superior characteristics in terms of voltage, efficiency, and lifetime compared to organic light-emitting devices using benzimidazole compounds (Comparative Examples 1-81 to 1-90).

[0544] Furthermore, it is known that when the above-mentioned chemical formula 1 contains substituents of dibenzofuran or naphthobenzofuran represented by chemical formula A1 (Examples 1-17 to 1-40 and Examples 1-57 to 1-80), the characteristics of low voltage, high efficiency and long life are enhanced.

[0545] Example 2-1.

[0546] A glass substrate coated with an ITO (indium tin oxide) film at a thickness of 1000 Å was immersed in distilled water containing detergent and ultrasonically washed. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the ultrasonic washing was repeated twice with distilled water for 10 minutes each time. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0547] On the prepared ITO transparent electrode, the following compound HI-A is thermally vacuum-deposited to a thickness of 600 Å to form a hole injection layer.

[0548] On the aforementioned hole injection layer, the following HAT compound 50Å and the following compound HT-A60Å are sequentially vacuum-deposited to form a first hole transport layer and a second hole transport layer.

[0549] Next, on the second hole transport layer, a light-emitting layer is formed by vacuum evaporation of compounds B1 and BD manufactured in Manufacturing Example 1-1 at a weight ratio of 25:1 with a film thickness of 200 Å.

[0550] On the aforementioned light-emitting layer, the following HB compound is vacuum-deposited to form a hole-blocking layer with a thickness of 50 Å, and the compound E1 manufactured in Manufacturing Example 2-1 is vacuum-deposited to form an electron injection and transport layer with a thickness of 300 Å.

[0551] On the aforementioned electron injection and transport layer, lithium fluoride (LiF) is deposited sequentially with a thickness of 10 Å and aluminum with a thickness of 1000 Å to form a cathode.

[0552] During the above process, the evaporation rate of organic materials was maintained at 0.4 Å / s to 0.9 Å / s, the evaporation rate of lithium fluoride at the cathode was maintained at 0.3 Å / s, and the evaporation rate of aluminum was maintained at 2 Å / s. The vacuum level was maintained at 1 × 10⁻⁶ during evaporation. -7 Up to 5×10 -5 This led to the creation of organic light-emitting devices.

[0553]

[0554] Examples 2-2 to 2-90.

[0555] Organic light-emitting devices were manufactured using the compounds listed in Table 2 below instead of compounds B1 and E1 in Example 2-1 above, except that the method was the same as that in Example 2-1 above.

[0556] Comparative Examples 2-1 to 2-80.

[0557] Organic light-emitting devices were manufactured using the compounds listed in Table 2 below instead of compounds B1 and E1 in Example 2-1 above, except that the method was the same as that in Example 2-1 above.

[0558] The organic light-emitting devices manufactured in Examples 2-1 to 2-80 and Comparative Examples 2-1 to 2-90 above were tested at 10 mA / cm². 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time (T90) at the given current density was measured relative to the initial brightness, which was 90%. The results are shown in Table 2 below.

[0559] [Table 2]

[0560]

[0561]

[0562]

[0563]

[0564]

[0565]

[0566] Comparing Examples 2-1 to 2-80 in Table 2 above with Comparative Examples 2-1 to 2-16, it can be confirmed that the organic light-emitting devices (Examples 2-1 to 2-80) using heterocyclic compounds of Formula 2 according to this specification exhibit significantly superior characteristics in terms of voltage, efficiency, and lifetime compared to organic light-emitting devices (Comparative Examples 2-1 to 2-16) using an organic light-emitting device with a structure in Formula 2 that does not contain a cyano group in its framework.

[0567] Comparing Examples 2-1 to 2-80 in Table 2 above with Comparative Examples 2-17 to 2-48, it can be confirmed that the organic light-emitting devices (Examples 2-1 to 2-80) using compounds of Formula 1 according to this specification exhibit significantly superior characteristics in terms of lifetime compared to organic light-emitting devices (Comparative Examples 2-17 to 2-48) using structures with the same skeleton as Formula 1 but without deuterium linked to anthracene.

[0568] Comparing Examples 2-1 to 2-80 in Table 2 above with Comparative Examples 2-49 to 2-80, it can be confirmed that the organic light-emitting devices (Examples 2-1 to 2-80) using compounds of Formula 1 according to this specification exhibit significantly superior characteristics in terms of lifetime compared to organic light-emitting devices (Comparative Examples 2-49 to 2-80) using structures with the same skeleton as Formula 1 but without the substitution of deuterium.

[0569] Comparing Examples 2-1 to 2-80 in Table 2 above with Comparative Examples 2-81 to 2-90, it can be confirmed that the organic light-emitting devices using compounds of chemical formula 2 according to this specification (Examples 2-1 to 2-80) exhibit significantly superior characteristics in terms of voltage, efficiency, and lifetime compared to organic light-emitting devices using benzimidazole compounds (Comparative Examples 2-81 to 2-90).

[0570] Furthermore, it is known that when the above-mentioned chemical formula 1 contains substituents of dibenzofuran or naphthobenzofuran represented by chemical formula A1 (Examples 2-17 to 2-40 and Examples 2-57 to 2-80), the characteristics of low voltage, high efficiency and long life are enhanced.

[0571] Example 3

[0572] The dipole moment (Debye) values ​​of compounds B1 to B4, B6 to B9, E1 to E5, and E8 according to one embodiment of this specification are shown in Table 3 below.

[0573] [Table 3]

[0574]

[0575] The above calculation of the dipole moment (Debye) was performed using Gauss 03, a quantum chemical calculation program manufactured by Gauss Corporation in the United States. Using density functional theory (DFT), the calculated value of the dipole moment was obtained for the structure optimized using B3LYP as the functional and 6-31G* as the basis function, using time-dependent density functional theory (TD-DFT).

[0576] The value of Equation 1 is obtained based on the above dipole moment value and is shown in Table 4 below.

[0577] [Formula 1]

[0578] |DM2-DM1| ≥ 3 Debye

[0579] In Equation 1 above,

[0580] DM1 is the dipole moment of the compound of chemical formula 1 above.

[0581] DM2 is the dipole moment of the compound of chemical formula 2 above.

[0582] [Table 4]

[0583]

[0584] It can be seen that due to the high dipole moment value of chemical formula 2, electron injection from the cathode is smooth, and when the dipole moment value satisfies formula 1, the efficiency and lifetime of organic light-emitting devices are improved.

Claims

1. An organic light-emitting device, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, The organic layer includes a light-emitting layer and a first organic layer. The first organic layer is disposed between the cathode and the light-emitting layer. The light-emitting layer comprises a compound of the following chemical formula 1, The first organic layer contains a compound of formula 2. Chemical Formula 1 In the chemical formula 1, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group. Ar1 and Ar2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group. D stands for deuterium. Chemical formula 2 In the chemical formula 2, L3 to L5 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group. Ar3 and Ar4 may be the same as or different from each other, and each is independently a cyano, a substituted or unsubstituted aryl, a heterocyclic group containing at least one of N and S, substituted or unsubstituted by one or more substituents selected from alkyl and aryl, or , Ar5 can be hydrogen, deuterium, cyano, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. At least one of Ar3 to Ar5 is a cyano group, or it contains one or more cyano groups as substituents. n1 is an integer from 0 to 7.

2. The organic light-emitting device according to claim 1, wherein, The compound of chemical formula 1 and the compound of chemical formula 2 satisfy the following formula 1: Formula 1 |DM2-DM1| ≥ 3 Debye In Equation 1, DM1 is the dipole moment of the compound of chemical formula 1. DM2 is the dipole moment of the compound of chemical formula 2.

3. The organic light-emitting device according to claim 1, wherein, Ar1 and Ar2 may be the same as or different from each other, and each may independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted naphthobenzofuranyl, or a substituted or unsubstituted naphthobenzothiophenyl.

4. The organic light-emitting device according to claim 1, wherein, Ar1 has the following chemical formula: Chemical formula A1 In the chemical formula A1, Y1 is either O or S. R1 to R8 may be the same as or different from each other, and each is independently a hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heterocyclic group, or may be combined with adjacent substituents to form a substituted or unsubstituted ring. One of R1 to R8 is connected to L1 of the chemical formula 1.

5. The organic light-emitting device according to claim 1, wherein, At least one of Ar3 to Ar5 is a cyano group, or has the following chemical formula 201: Chemical formula 201 In the chemical formula 201, Ar6 is a substituted or unsubstituted divalent to tetravalent aryl group, or a substituted or unsubstituted divalent to tetravalent heterocyclic group. m1 is an integer from 1 to 3. The dashed line connects to the chemical formula 2.

6. The organic light-emitting device according to claim 1, wherein, At least one of Ar3 to Ar5 is a cyano group, or any one of the following chemical formulas 202 to 204: Chemical formula 202 Chemical formula 203 Chemical formula 204 In the chemical formulas 202 to 204, m1 is an integer from 1 to 3. Ar61 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group. R21 is hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. R22 and R23 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. r21 is an integer from 0 to 4, and r21' and r21'' are each integers from 0 to 6. When r21, r21', and r21'' are each 2 or more, R21 may be the same or different from each other. The dashed line connects to the chemical formula 2.

7. The organic light-emitting device according to claim 1, wherein, Ar3 and Ar4 may be the same as or different from each other, and each is independently selected from one of the following groups 1' or 2'. Group 1' Group 2' In groups 1' and 2', The dashed line indicates the position where it connects to chemical formula 2. Y3 is either S or NR14. X1 to X5 may be the same as or different from each other, and each is independently N or CR15. At least one of X1 to X5 is N. R11 and R12 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic. R13 to R15 may be the same as or different from each other, and each may be independently hydrogen, alkyl, or aryl. Cy1 is a monocyclic or polycyclic aromatic hydrocarbon ring, or a monocyclic or polycyclic aromatic heterocycle. The structure of group 1' is substituted or unsubstituted by deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic groups, and Ar5 is hydrogen, deuterium, cyano, or selected from one of the following groups: Group 1 Group 2 In groups 1 and 2, The dashed line indicates the position where it connects to chemical formula 2. Y3 is O, S, or NR14. X1 to X5 may be the same as or different from each other, and each is independently N or CR15. At least one of X1 to X5 is N. R11 to R15 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic. Cy1 is a monocyclic or polycyclic aromatic hydrocarbon ring, or a monocyclic or polycyclic aromatic heterocycle. The structures of groups 1 and 2 are substituted or unsubstituted by deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic groups.

8. The organic light-emitting device according to claim 1, wherein, 100% of the chemical formula 1 is deuterated.

9. The organic light-emitting device according to claim 1, wherein, Chemical Formula 1 is selected from one of the following compounds: 。 10. The organic light-emitting device according to claim 1, wherein, Chemical Formula 1 is selected from one of the following compounds: 。 11. The organic light-emitting device according to claim 1, wherein, Chemical Formula 2 is selected from one of the following compounds: 。 12. The organic light-emitting device according to claim 1, wherein, The first organic layer is configured to be in direct contact with the cathode.

13. The organic light-emitting device according to claim 1, wherein, The organic layer includes two or more light-emitting layers, one of which contains a compound of chemical formula 1.

14. The organic light-emitting device according to claim 13, wherein, The maximum emission peaks of the two or more light-emitting layers are different from each other.

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