Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device comprising the same. The compound described in the specification can be used as a material for an organic layer of an organic light-emitting device. Specifically, the compound described in the specification can be used as a material for a light-emitting layer. The compound described in the present specification is included in an organic light-emitting device and can improve device characteristics such as low driving voltage, excellent efficiency characteristics, and / or excellent lifespan characteristics.

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2024-0114074, filed with the Korean Patent Office on August 26, 2024, the entire contents of which are contained in this specification.

[0002] This specification relates to compounds and organic light-emitting devices containing them. 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.

[0005] Existing technical documents

[0006] Patent documents

[0007] (Patent Document 1) Korean Patent Publication No. 10-2017-0036641 Summary of the Invention

[0008] Technical issues

[0009] This application provides compounds and organic light-emitting devices containing the same.

[0010] Solution to the problem

[0011] One embodiment of this specification provides a compound of chemical formula 1:

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] L1 is a directly bonded, substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0016] A is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted silyl group, or a substituted or unsubstituted heteroaryl group containing O or S.

[0017] Ar1 is a substituted or unsubstituted aryl group.

[0018] R1 to R3 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0019] R4 is either hydrogen or deuterium.

[0020] r1 to r3 are each integers from 1 to 4, r4 is an integer from 1 to 3, and when r1 to r4 are 2 or more, the substituents in each parenthesis are the same or different from each other.

[0021] Another embodiment of this specification provides an organic light-emitting device, comprising: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contain the aforementioned compound.

[0022] Invention Effects

[0023] The compound according to one embodiment of the present invention can be used as a material for the organic layer of an organic light-emitting device.

[0024] The compound according to a specific embodiment of the present invention can be used as a material for the light-emitting layer of an organic light-emitting device.

[0025] The compound according to one embodiment of the present invention can be included in an organic light-emitting device to improve device characteristics such as lower driving voltage, excellent efficiency characteristics and / or excellent lifetime characteristics. Attached Figure Description

[0026] Figures 1 to 3 Examples of organic light-emitting devices according to several embodiments of the present invention are illustrated.

[0027] Figure 4 MS plot of compound A.

[0028] Symbol Explanation

[0029] 1: Substrate

[0030] 2: Anode

[0031] 3: Emissive layer

[0032] 4: Cathode

[0033] 5: Hole injection layer

[0034] 6: Hole transport layer

[0035] 7: Emissive layer

[0036] 8: Electron transport layer

[0037] 9: Electron blocking layer

[0038] 10: Hole-blocking layer

[0039] 11: Electron Injection and Transport Layer Detailed Implementation

[0040] The following is a more detailed description of this instruction manual.

[0041] This specification provides for compounds of the above chemical formula 1.

[0042] According to one embodiment of this specification, Chemical Formula 1 contains a biscarbazole structure, which increases the LUMO energy level of the compound, thereby preventing host-guest electrostatic coupling in the organic layer of the organic light-emitting device containing it. Furthermore, the phenyl and phenylene-carbazole bound at specific positions of the biscarbazole participate in the conjugation system through a hyperconjugation effect, thus possessing structural features that stabilize the excited and polaronic states of Chemical Formula 1. Therefore, including Chemical Formula 1 in the organic layer of an organic light-emitting device enables improved efficiency, lower driving voltage, and improved lifetime characteristics.

[0043] 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.

[0044] 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.

[0045] In this specification, the meaning of a specific substance A being contained in layer B includes i) the case where one or more substances A are contained in a single layer of layer B, and ii) the case where layer B consists of one or more layers and substances A are contained in one or more layers of multiple layers of layer B.

[0046] In this specification, the meaning of a specific substance A being contained in layer C or layer D is all of the following: i) substance A is contained in one or more layers of layer C, or ii) substance A is contained in one or more layers of layer D, or iii) substance A is contained in one or more layers of layer C and one or more layers of layer D.

[0047] In this specification, n-type refers to a substance that can remove electrons from the matrix material (the material of the organic layer), and generally, known substances can be used, but are not limited to these. That is, n-type can be defined as a substance that has the property of donating electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix. Conversely, p-type refers to substances that, when a layer is composed solely of p-type material, accept electrons from the HOMO (highest occupied molecular orbital) energy level of the adjacent cathode-directed material, generating holes in the adjacent cathode-directed material; or, when p-type material is doped into any matrix, accept electrons from the HOMO of the matrix material, generating an equal number of holes in the matrix's HOMO. Therefore, when a layer is formed solely of p-type material, the closer the HOMO of the cathode-directed material is to the LUMO of the p-type material, the easier it is for the p-type material to steal electrons from the HOMO of the adjacent layer, generating holes in the HOMO of the adjacent layer. Furthermore, when p-type material is doped into any matrix, the closer the LUMO of the p-type material is to the HOMO of the matrix, the easier it is for the p-type material to steal electrons, generating holes in the matrix.

[0048] In this specification, the term "substitution" refers to the replacement of hydrogen atoms on carbon atoms of 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 two or more substituents are substituted, the two or more substituents can be the same or different from each other.

[0049] In this specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, halogen groups, nitrile (-CN), nitro, hydroxyl, alkyl, cycloalkyl, alkoxy, phosphine oxide, aryloxy, and alkylthio. aryl thiols alkylsulfonyl arylsulfonyl The substituent may be one or more of the following: alkenyl, silyl, boryl, amino, aryl, and heterocyclic groups; or may be substituted by a substituent formed by linking two or more of the substituents exemplified above; or may not have any substituents. For example, "a substituent formed by linking two or more substituents" may be biphenyl. That is, biphenyl may be aryl, or it may be interpreted as a substituent formed by linking two phenyl groups.

[0050] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, nitrile groups, silyl groups, alkoxy groups, aryl groups, alkyl groups, aryl groups, and heterocyclic groups, or substituted by two or more substituents linked together from the substituents exemplified above, or not having any substituents.

[0051] In this specification, the term "substituted or unsubstituted" means substituted by one or two or more substituents selected from deuterium, alkyl, aryl, and heterocyclic groups, or substituted by two or more substituents linked together from the substituents exemplified above, or not having any substituents.

[0052] Examples of the above substituents are described below, but are not limited thereto.

[0053] Examples of halogen groups in this specification include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0054] In this specification, silane may 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. Specific examples of the aforementioned silane include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, biphenyldiphenylsilane, and phenylsilane, but are not limited to these. The number of carbon atoms in the aforementioned silane can be from 3 to 60, but is not limited to this.

[0055] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. In one embodiment, the alkyl group has 1 to 30 carbon atoms. In another embodiment, the alkyl group has 1 to 20 carbon atoms. In yet another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited to these.

[0056] In this specification, the alkoxy group can be linear, linear, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, etc., but is not limited to these.

[0057] The alkyl, alkoxy, and other substituents containing alkyl moiety described in this specification include all linear or linear forms.

[0058] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. In one embodiment, the alkenyl group has 2 to 20 carbon atoms. In another embodiment, the alkenyl group has 2 to 10 carbon atoms. In yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc., but are not limited to these.

[0059] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0060] In this specification, the amino group is -NH2, and the amino group may be substituted with alkyl, aryl, heterocyclic, alkenyl, cycloalkyl, and combinations thereof. The number of carbon atoms in the substituted amino group is not particularly limited, but is preferably 1 to 30. In one embodiment, the number of carbon atoms in the amino group is 1 to 20. In another embodiment, the number of carbon atoms in the amino group is 1 to 10. Specific examples of substituted amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthraceneamino, dibenzofuranylphenylamino, 9-methylanthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, diphenylamino, etc., but are not limited to these.

[0061] In this specification, the aryl group is not particularly limited, but is preferably composed of 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. In one embodiment, the aryl group has 6 to 30 carbon atoms. In another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, tetraphenyl, etc., but is not limited to these. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes methyl, fluorene, triphenylene, etc., but is not limited to these.

[0062] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure.

[0063] When the aforementioned fluorene group is replaced, it can become Isospirofluorene group; (9,9-dimethylfluorene) and Substituted fluorenyl groups such as (9,9-diphenylfluorenyl) are used. However, this is not a limitation.

[0064] In this specification, the aryl group in the aryl group can be described in the above description of the aryl group.

[0065] In this specification, a heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. In one embodiment, the heterocyclic group has 2 to 30 carbon atoms. In another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of heterocyclic groups include pyridyl, pyrroloyl, pyrimidinyl, quinolinyl, pyridazinyl, furanyl, thiopheneyl, imidazoyl, pyrazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, naphthobenzofuranyl, benzonaphthothiopheneyl, indenzocarbazoleyl, triazinyl, etc., but are not limited to these.

[0066] In this specification, heteroaryl refers to aromatic compounds; otherwise, the above description of heterocyclic groups applies.

[0067] In this specification, the ester group refers to -R701-C(=O)-OR702-.

[0068] In this specification, allyl refers to R(801)2C=CH-C(R802)2-.

[0069] R701, R702, R801 and R802 are the same as or different from each other, and are each independently hydrogen, alkyl, aryl or heteroaryl, and the definitions of alkyl, aryl and heteroaryl are the same as those of the substituents exemplified above.

[0070] In this specification, alkylene refers to a group with two bonding sites on an alkyl group, i.e., a divalent group. These groups, apart from being divalent, are subject to the same description of alkyl groups as those described above.

[0071] In this specification, a trivalent alkylene group refers to a group with three bonding positions on an alkyl group, i.e., a trivalent group. These groups, apart from being trivalent themselves, can be described as alkyl groups as described above.

[0072] In this specification, arylene refers to a group with two bonding sites on an aryl group, i.e., a divalent group. These groups, except that they are each divalent, can be described in the same way as the aryl groups described above. For example, phenylene is a divalent phenyl group.

[0073] In this specification, a trivalent aryl group refers to a group with three bonding positions on an aryl group, i.e., a trivalent group. Apart from being trivalent groups themselves, they are subject to the above description of aryl groups.

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

[0075] In this specification, a divalent alkenyl group refers to a group with two bonding sites on the alkenyl group, i.e., a divalent group. These groups, apart from being divalent themselves, are subject to the above description of alkenyl groups.

[0076] In this specification, a divalent allyl group refers to a group with two bonding sites on the allyl group, i.e., a divalent group. These groups, apart from being divalent themselves, are subject to the above description of the allyl group.

[0077] In this specification, [] Dn The parentheses indicate that the structure contains deuterium. Here, D represents deuterium, and n represents the number of deuteriums. That is, Dn represents the number of deuteriums contained in the structure within the parentheses, and its value is an integer. For example, 1 ≤ Dn ≤ 32 indicates that it contains 1 to 32 deuteriums. As an example, the following structures contain 1 to 32 deuteriums.

[0078]

[0079] In this specification, unless otherwise defined, all technical and scientific terms used have the same meaning as commonly understood by those skilled in the art. Methods and materials similar to or equivalent to those described herein may be used to implement or test embodiments of the invention, but suitable methods and materials are described later. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, unless a specific passage is mentioned, this specification, including its definitions, takes precedence. Furthermore, materials, methods, and embodiments are illustrative only and not intended to be limiting.

[0080] The following is a detailed description of the compound of chemical formula 1.

[0081] In one embodiment of this specification, the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-3.

[0082] [Chemical Formula 1-1]

[0083]

[0084] [Chemical Formula 1-2]

[0085]

[0086] [Chemical Formulas 1-3]

[0087]

[0088] In the above chemical formulas 1-1 to 1-3,

[0089] L1, A, Ar1, R1 to R4 and r1 to r4 are the same as those defined in Chemical Formula 1 above.

[0090] In one embodiment of this specification, L1 is a directly bonded, substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0091] In one embodiment of this specification, L1 is a directly bonded, deuterated or unsubstituted phenylene, or a deuterated or unsubstituted biphenylene.

[0092] In one embodiment of this specification, A is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted silyl group, or a heteroaryl group containing O or S with 2 to 30 carbon atoms.

[0093] In one embodiment of this specification, A is a deuterated or unsubstituted phenyl; a deuterated or unsubstituted biphenyl; a deuterated or unsubstituted terphenyl; a deuterated or unsubstituted tetraphenyl; a silyl group substituted or unsubstituted with one or more of deuterium and aryl groups; or a deuterated or unsubstituted heteroaryl group containing O or S.

[0094] In one embodiment of this specification, A is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted silyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0095] In one embodiment of this specification, A is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted terphenyl, a deuterated or unsubstituted tetraphenyl, a silyl group substituted or unsubstituted with one or more of deuterium and aryl, a deuterated or unsubstituted dibenzofuranyl, or a deuterated or unsubstituted dibenzothiopheneyl.

[0096] In one embodiment of this specification, Ar1 is a substituted or unsubstituted aryl group.

[0097] In one embodiment of this specification, Ar1 is an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0098] In one embodiment of this specification, Ar1 is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, or a substituted or unsubstituted naphthyl.

[0099] In one embodiment of this specification, Ar1 is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted terphenyl, or a deuterated or unsubstituted naphthyl.

[0100] In one embodiment of this specification, Ar1 is a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.

[0101] In one embodiment of this specification, Ar1 is a phenyl group that is either deuterated or unsubstituted, or a biphenyl group that is either deuterated or unsubstituted.

[0102] In one embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0103] In one embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, or substituted or unsubstituted aryl with 6 to 30 carbon atoms.

[0104] In one embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.

[0105] In one embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen, deuterium, a phenyl substituted or unsubstituted with deuterium, or a biphenyl substituted or unsubstituted with deuterium.

[0106] In one embodiment of this specification, the deuterium substitution rate of the compound of Formula 1 is 0% to 100%.

[0107] In one embodiment of this specification, the deuterium substitution rate of the compound of chemical formula 1 is 10% or more.

[0108] In one embodiment of this specification, the deuterium substitution rate of the compound of chemical formula 1 is 20% or more.

[0109] In one embodiment of this specification, the deuterium substitution rate of the compound of chemical formula 1 is 40% or more.

[0110] In one embodiment of this specification, the deuterium substitution rate of the compound of chemical formula 1 is 60% or more.

[0111] In this specification, "deuterium substitution", "containing deuterium", "deuteration" or "deuteration" means that hydrogen at a substituted position in a compound is replaced by deuterium.

[0112] In this specification, "per-deuterated" refers to a compound or group in which all hydrogen atoms in the molecule are replaced by deuterium, and has the same meaning as "100% deuterated".

[0113] In this specification, "X% deuterated", "degree of deuteration X%", or "deuteration rate X%" means that X% of the hydrogens at the substituted positions in the structure are replaced with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" of the aforementioned dibenzofuran, "degree of deuteration 25%" of the aforementioned dibenzofuran, or "deuteration rate 25%" of the aforementioned dibenzofuran means that 2 out of the 8 hydrogens at the substituted positions in the aforementioned dibenzofuran are replaced with deuterium.

[0114] In this specification, "degree of deuteration" or "deuteration substitution rate" can be determined by nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1The assay was confirmed using known methods such as ¹H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0115] Specifically, through nuclear magnetic resonance spectroscopy (NMR spectroscopy) 1 When analyzing "degree of deuteration" or "deuteration substitution rate" using ¹H NMR, DMF (dimethylformamide) can be added as an internal standard. 1 The integration ratio on H NMR is used to calculate the degree of deuteration or the rate of deuteration substitution from the total peak.

[0116] Additionally, when analyzing "degree of deuteration" or "deuteration substitution rate" using TLC / MS (thin-layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum value (intermediate value) of the molecular weight distribution at the end of the reaction. For example, when analyzing the degree of deuteration of compound A below, the molecular weight of the starting material is 506. Figure 4 In the MS chart, when the maximum molecular weight (median value) of compound A is 527, 21 of the 26 substituted hydrogen positions in the starting material are replaced with deuterium, so it can be calculated that about 81% of the hydrogen is deuterated.

[0117]

[0118] In one embodiment of this specification, the compound is any one of the following structures.

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156] In the above structure, Dn is the number of deuterium atoms contained in the compound.

[0157] In this specification, compounds with various band gaps can be synthesized by introducing various substituents into the core structure as described above. Furthermore, in this invention, the HOMO and LUMO energy levels of the compounds can also be tuned by introducing various substituents into the core structure as described above.

[0158] Furthermore, by introducing various substituents into the core structure described above, compounds possessing the inherent properties of the introduced substituents can be synthesized. For example, by introducing substituents primarily used in hole injection layer materials, hole transport layer materials, electron blocking layer materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the aforementioned core structure, substances satisfying the requirements of each organic layer can be synthesized.

[0159] One embodiment of this specification provides an organic light-emitting device, comprising: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contain the aforementioned compound.

[0160] Specifically, the aforementioned organic light-emitting device includes an anode, a cathode, and one or more organic layers including a light-emitting layer disposed between the anode and the cathode, wherein one or more of the organic layers contains a compound of the aforementioned chemical formula 1.

[0161] The organic light-emitting device described in this specification utilizes the aforementioned compound to form one or more organic layers. Alternatively, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0162] In one embodiment of this specification, the thickness of the organic layer comprising the compound of formula 1 is [missing information]. to Preferred to More preferably to

[0163] The aforementioned compounds can be used to form organic layers not only through vacuum evaporation but also through solution coating in the fabrication of organic light-emitting devices. Here, solution coating refers to methods such as spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating, but is not limited to these.

[0164] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. This can be achieved by depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation to form the anode. Then, an organic layer comprising a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, and an electron transport layer is formed on the anode. Finally, a material suitable for use as the cathode is deposited onto the organic layer. Alternatively, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate. Furthermore, the compound of Formula 1 described above can be used to form the organic layer not only by vacuum evaporation but also by solution coating when manufacturing the organic light-emitting device. Here, the so-called solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited to these.

[0165] In one embodiment of this specification, the aforementioned organic layer can be formed as a single-layer structure or as a multilayer structure with two or more organic layers stacked on top of each other. When the aforementioned organic light-emitting device includes a plurality of organic layers, for example, the organic layers can be a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer. However, the structure of the organic light-emitting device is not limited to this, and may include fewer or more organic layers.

[0166] The aforementioned organic layers can be formed from the same or different substances. Furthermore, the aforementioned organic layers can be manufactured in smaller quantities using various polymer materials and solvent processes other than vapor deposition, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0167] In one embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the aforementioned compound.

[0168] In one embodiment of this specification, the light-emitting layer is a blue light-emitting layer.

[0169] In one embodiment of this specification, the maximum emission wavelength of the light-emitting layer is 420 nm to 495 nm.

[0170] In one embodiment of this specification, the aforementioned organic layer includes a hole-blocking layer, an electron transport layer, an electron injection layer, or an electron injection and transport layer. In this case, the aforementioned hole-blocking layer, electron transport layer, electron injection layer, or electron injection and transport layer may or may not contain the aforementioned compound.

[0171] In one embodiment of this specification, the aforementioned organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, or a hole injection and transport layer. In this case, the aforementioned hole blocking layer, electron transport layer, electron injection layer, or hole injection and transport layer may or may not contain the aforementioned compound.

[0172] In one embodiment of this specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, wherein the hole injection layer, hole transport layer, or hole injection and transport layer contains the aforementioned compound.

[0173] In one embodiment of this specification, the organic light-emitting device includes an anode; a cathode; and a light-emitting layer disposed between the anode and the cathode, and further includes a single organic layer between the light-emitting layer and the anode, wherein one or more of the light-emitting layer and the single organic layer contain the aforementioned compound.

[0174] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, and further includes a single-layer organic layer between the light-emitting layer and the anode, wherein the light-emitting layer contains the aforementioned compound.

[0175] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, and further includes multiple organic layers between the light-emitting layer and the anode, wherein one or more of the light-emitting layer and the multiple organic layers contain the aforementioned compound.

[0176] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, and further includes a multilayer organic layer between the light-emitting layer and the anode, wherein the light-emitting layer contains the aforementioned compound.

[0177] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. It also includes one or more of a hole injection layer, a hole transport layer, and an electron blocking layer between the light-emitting layer and the anode. One or more of the light-emitting layer, hole injection layer, hole transport layer, and electron blocking layer contain the aforementioned compound.

[0178] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, and further includes one or more of a hole injection layer, a hole transport layer, and an electron blocking layer between the light-emitting layer and the anode, wherein the light-emitting layer contains the aforementioned compound.

[0179] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, including a hole injection layer, a hole transport layer, and an electron blocking layer between the anode and the light-emitting layer, wherein the light-emitting layer contains the aforementioned compound.

[0180] In one embodiment of this specification, the organic light-emitting device comprises, in sequence, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, and a cathode, wherein the light-emitting layer contains the aforementioned compound. In this case, additional organic layers may also be disposed between the aforementioned layers.

[0181] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. The light-emitting layer and the cathode also include a single organic layer, and one or more of the light-emitting layer and the single organic layer contain the aforementioned compound.

[0182] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. The light-emitting layer and the cathode also include a single organic layer, and the light-emitting layer contains the aforementioned compound.

[0183] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. The light-emitting layer and the cathode further include multiple organic layers, and one or more of the light-emitting layer and the multiple organic layers contain the aforementioned compound.

[0184] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. The light-emitting layer and the cathode further include multiple organic layers, and the light-emitting layer contains the aforementioned compound.

[0185] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. The cathode and the light-emitting layer further include one or more of a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer. One or more of the light-emitting layer, hole blocking layer, electron injection layer, electron transport layer, and electron injection and transport layer contain the aforementioned compound.

[0186] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. The cathode and the light-emitting layer further include one or more of a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer. The light-emitting layer contains the aforementioned compound.

[0187] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. The cathode and the light-emitting layer include a hole-blocking layer and an electron injection and transport layer. The light-emitting layer contains the aforementioned compound.

[0188] In one embodiment of this specification, the organic light-emitting device is configured with an anode, a light-emitting layer, a hole-blocking layer, an electron injection and transport layer, and a cathode sequentially disposed therefrom, wherein the light-emitting layer comprises the aforementioned compound. In this case, additional organic layers may also be disposed between the aforementioned layers.

[0189] In one embodiment of this specification, the organic light-emitting device is a structure in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron injection and transport layer, and a cathode are sequentially stacked, and the light-emitting layer contains the aforementioned compound.

[0190] For example, the structure of the organic light-emitting device described in this specification can have the following characteristics: Figures 1 to 3 The structure shown is not limited to this.

[0191] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

[0192] Figure 2 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.

[0193] Figure 3 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light-emitting layer 7, a hole blocking layer 10, an electron injection and transport layer 11, and a cathode 4.

[0194] Specifically, in addition to the structure shown in the figure above, the organic light-emitting device may have, for example, the layered structure shown below, but is not limited to this.

[0195] (1) Anode / hole transport layer / light-emitting layer / cathode

[0196] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0197] (3) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0198] (4) Anode / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0199] (5) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode

[0200] (6) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0201] (7) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0202] (8) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0203] (9) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0204] (10) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0205] (11) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0206] (12) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0207] (13) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0208] (14) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0209] (15) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0210] In one embodiment of this specification, the “electron transport layer / electron injection layer” can be replaced by “electron injection and transport layer” or “layer that performs both electron injection and electron transport simultaneously”. For example, the above (15) can be an organic light-emitting device having a stacking order of “anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode”.

[0211] In one embodiment of this specification, the aforementioned “hole injection layer / hole transport layer” can be replaced by “hole injection and transport layer” or “layer that performs hole injection and hole transport simultaneously”. For example, the aforementioned (15) can be an organic light-emitting device having a stacking order of “anode / hole injection and transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode”.

[0212] The anode described above is the electrode for injecting holes. As the anode material, it is generally preferred to be a material with a high work function in order to enable holes to be smoothly injected into the organic layer. Specific examples of anode materials that can be used in this invention 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 are not limited to these.

[0213] The cathode described above is the electrode into which electrons are injected. As a cathode material, a material with a low work function is preferred in order to facilitate the injection of electrons into the organic layer. Specific examples of cathode materials that can be used in this invention include metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; multilayer materials such as LiF / Al or LiO2 / Al; but are not limited to these.

[0214] The aforementioned hole injection layer facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is one that can readily inject holes from the anode at low voltage; preferably, the HOMO (highest occupied molecular orbital) of the hole injection material lies between the work function of the anode and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine compounds, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, perylene compounds, benzonitrile compounds, anthraquinones, polyaniline, and polythiophene-based conductive polymers.

[0215] Specifically, aryl amine compounds and benzonitrile compounds can be used in the aforementioned hole injection layer. More specifically, one or more of the following can be used: aryl amine compounds substituted with carbazole groups and benzonitrile compounds substituted with halogen groups, but this is not a limitation.

[0216] In one embodiment of this specification, the hole injection layer comprises a compound represented by the following chemical formula HI-1.

[0217] [Chemical formula HI-1]

[0218]

[0219] In the above chemical formula HI-1,

[0220] R300 to R302 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or may be combined with adjacent groups to form substituted or unsubstituted rings.

[0221] r300 is an integer from 1 to 5. When r300 is 2 or more, two or more of the above R300 values ​​are the same or different from each other.

[0222] r301 is an integer from 1 to 5. When r301 is 2 or more, two or more of the above R301 are the same or different from each other.

[0223] In one embodiment of this specification, R302 is selected from any one of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, and combinations thereof.

[0224] In one embodiment of this specification, R302 is selected from carbazolyl, phenyl, biphenyl, triphenylene, and combinations thereof.

[0225] In one embodiment of this specification, R300 and R301 may be the same as or different from each other, each being independently a substituted or unsubstituted aryl group, or combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an aryl or alkyl group.

[0226] In one embodiment of this specification, R300 and R301 may be the same as or different from each other, each being independently phenyl or biphenyl, or combined with adjacent groups to form indene substituted with phenyl or methyl groups.

[0227] In one embodiment of this specification, the above chemical formula HI-1 is any one of the following compounds.

[0228]

[0229] In one embodiment of this specification, the hole injection layer comprises a compound represented by the chemical formula HI-2.

[0230] [Chemical formula HI-2]

[0231]

[0232] In the above chemical formula HI-2,

[0233] R401 to R403 may be the same as or different from each other, and each is an independent halogen group.

[0234] When r401 to r403 are integers from 1 to 4, and r401 to r403 are 2 or more, the substituents in each parenthesis are the same or different from each other.

[0235] In one embodiment of this specification, R401 to R403 are F.

[0236] In one embodiment of this specification, the above chemical formula HI-2 comprises the following compound.

[0237]

[0238] In one embodiment of this specification, the hole injection layer comprises the chemical formulas HI-1 and HI-2.

[0239] In one embodiment of this specification, the hole injection layer comprises the above-mentioned chemical formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1.

[0240] In one embodiment of this specification, the thickness of the hole injection layer can be from 1 nm to 150 nm. When the thickness of the hole injection layer is 1 nm or more, it has the advantage of preventing a decrease in hole injection characteristics, and when it is 150 nm or less, it has the advantage of preventing an increase in driving voltage to improve hole migration when the thickness of the hole injection layer is too thick.

[0241] The aforementioned hole transport layer facilitates hole transport. The hole transport material is capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer; materials with high hole mobility are suitable. Specific examples of hole transport materials include arylamine compounds, carbazole compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these. Specifically, carbazole compounds substituted with arylamine groups can be used in the aforementioned hole transport layer, but are not limited to these.

[0242] In one embodiment of this specification, the hole transport layer comprises a compound represented by the chemical formula HI-1.

[0243] 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. When the electron blocking layer includes an electron blocking layer comprising a compound of Formula 1 according to one embodiment of this specification, or other electron blocking layers, known materials can be used without limitation, including but not limited to the substances exemplified in the description of the hole injection layer. The aforementioned electron blocking layer can be formed between the light-emitting layer and the hole transport layer, 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.

[0244] In one embodiment of this specification, a carbazole-based compound may be used in the electron blocking layer. Specifically, a carbazole-based compound substituted with an arylamine group may be used, but it is not limited thereto.

[0245] In one embodiment of this specification, the electron blocking layer comprises a compound represented by the chemical formula HI-1.

[0246] The aforementioned luminescent layer can emit red, green, or blue light and can be formed from phosphorescent or fluorescent substances. The luminescent substance is capable of receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining them to emit light in the visible light region. Preferably, it is a substance with high quantum efficiency for fluorescence or phosphorescence. Examples of such luminescent substances include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds of the azole, benzothiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV) polymers; spirocyclic compounds; polyfluorene, fluorene, etc., but not limited to these.

[0247] The main materials for the luminescent layer include aromatic fused-ring derivatives or heterocyclic compounds. For example, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited to these. Specifically, compounds of Chemical Formula 1 of the present invention can be used as the main body of the above-mentioned luminescent layer, but are not limited to these.

[0248] When the luminescent layer emits red light, phosphorescent dopants such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum) can be used; or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the emitting layer emits green light, phosphorescent materials such as Ir(ppy)3 (tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used as luminescent dopants, but these are not limited to these. When the emitting layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used as luminescent dopants; or fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene aryl (DSA), pyrene compounds, PFO polymers, and PPV polymers can be used, but these are not limited to these. Specifically, pyrene compounds can be used as the above dopants, but these are not limited to these.

[0249] In one embodiment of this specification, the light-emitting layer comprises a compound of chemical formula 1.

[0250] In one embodiment of this specification, the light-emitting layer containing the above-described compound may contain only a single substance, but may also contain other substances. For example, the above-described compound may act as the main component in the light-emitting layer, in which case other dopants may also be included.

[0251] In one embodiment of this specification, the light-emitting layer comprises a body, and the body comprises the compound described above.

[0252] In one embodiment of this specification, the organic layer includes a light-emitting layer, wherein the light-emitting layer contains the compound as a p-type host of the light-emitting layer.

[0253] In one embodiment of this specification, the organic layer includes a light-emitting layer, wherein the light-emitting layer contains the compound as a p-type phosphorescent host for the light-emitting layer.

[0254] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains the compound as a host and other host components.

[0255] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains the compound as a host, and also contains other hosts and dopants.

[0256] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains the compound as a first host and also contains a second host.

[0257] In one embodiment of this specification, the first body is a p-type body and the second body is an n-type body.

[0258] In one embodiment of this specification, the first body is a p-type phosphorescent body and the second body is an n-type phosphorescent body.

[0259] In one embodiment of this specification, the light-emitting layer comprises a first body and a second body in a weight ratio of 2:8 to 8:2. The first subject mentioned above is a compound of chemical formula 1.

[0260] In one embodiment of this specification, the light-emitting layer comprises a first body and a second body in a 1:1 weight ratio, wherein the first body is a compound of the aforementioned chemical formula 1.

[0261] In one embodiment of this specification, the second component is a dibenzofuran compound.

[0262] In one embodiment of this specification, the second component is a triazine compound. Specifically, it is a triazine compound substituted with a carbazole group.

[0263] In one embodiment of this specification, the light-emitting layer comprises a compound with the chemical formula HB-1.

[0264] [Chemical formula HB-1]

[0265]

[0266] In the aforementioned HB-1,

[0267] Q1 to Q3 are either N or CR, and at least one of Q1 to Q3 is N.

[0268] L701 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0269] R and T1 to T3 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0270] In one embodiment of this specification, Q1 to Q3 are N.

[0271] In one embodiment of this specification, the L701 is a directly bonded, substituted, or unsubstituted aryl group with 6 to 30 carbon atoms.

[0272] In one embodiment of this specification, L701 is directly bonded or aryl.

[0273] In one embodiment of this specification, the L701 is a directly bonded or arylene group having 6 to 30 carbon atoms.

[0274] In one embodiment of this specification, L701 is directly bonded or phenylene.

[0275] In one embodiment of this specification, T1 to T3 may be the same as or different from each other, and each may be a substituted or unsubstituted heteroaryl group.

[0276] In one embodiment of this specification, T1 to T3 may be the same as or different from each other, and each is independently a monocyclic or polycyclic heteroaryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0277] In one embodiment of this specification, T1 to T3 may be the same as or different from each other, and each is independently a heteroaryl group.

[0278] In one embodiment of this specification, T1 to T3 may be the same as or different from each other, and each is independently a monocyclic or polycyclic heteroaryl group with 6 to 30 carbon atoms.

[0279] In one embodiment of this specification, T1 to T3 are carbazole groups.

[0280] In one embodiment of this specification, the above chemical formula HB-1 comprises the following compound.

[0281]

[0282] In one embodiment of this specification, the light-emitting layer comprises a compound of chemical formula 1 as a first body and a compound of chemical formula HB-1 as a second body.

[0283] In one embodiment of this specification, the light-emitting layer further comprises a fluorescent dopant or a phosphorescent dopant.

[0284] At this point, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used as the dopant; or fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene arylene (DSA), PFO-based polymers, PPV-based polymers, anthracene compounds, pyrene compounds, and boron compounds can be used, but these are not limited to these.

[0285] In one embodiment of this specification, the light-emitting layer further comprises a phosphorescent dopant.

[0286] In one embodiment of this specification, the dopant in the light-emitting layer comprises 1 to 50 parts by weight relative to 100 parts by weight of the main body.

[0287] In one embodiment of this specification, the dopant is a metal coordination compound.

[0288] In one embodiment of this specification, the dopant is a platinum coordination compound.

[0289] In one embodiment of this specification, the dopant is an iridium coordination compound.

[0290] In one embodiment of this specification, the dopant is of the following chemical formula D-1 or D-2, but is not limited thereto.

[0291] [Chemical Formula D-1]

[0292]

[0293] [Chemical formula D-2]

[0294]

[0295] In the above chemical formulas D-1 and D-2,

[0296] M is a transition metal.

[0297] Z1, Z3, Z5, Z6, K1, K2, and K3 may be the same as or different from each other, and each is independently a directly bonded, O, S, divalent ester group, substituted or unsubstituted alkylene group, substituted or unsubstituted divalent alkenyl group, substituted or unsubstituted diallyl group, substituted or unsubstituted arylene group, or substituted or unsubstituted heteroarylene group.

[0298] Z2 and Z4 may be the same as or different from each other, and each is independently a directly bonded, N, substituted or unsubstituted trivalent alkylene, substituted or unsubstituted trivalent aryl, or substituted or unsubstituted trivalent heteroaryl.

[0299] n is 1 or 2. When n is 2, the structures inside the parentheses are the same or different from each other.

[0300] In one embodiment of this specification, the dopant may be selected from the following structural formulas, but is not limited thereto.

[0301]

[0302]

[0303]

[0304]

[0305] A hole-blocking layer can also be disposed between the cathode and the light-emitting layer. This hole-blocking layer prevents holes from reaching the cathode and can typically be formed under the same conditions as the electron injection layer. Specific examples of hole-blocking materials include... The following are permitted derivatives, but not limited to: diazole derivatives, triazole derivatives, triazine derivatives, phenanthroline derivatives, BCP, and aluminum complexes. Specifically, triazine derivatives may be used, but are not limited to these.

[0306] In one embodiment of this specification, the hole-blocking layer comprises a compound of the chemical formula HB-1.

[0307] The aforementioned electron transport layer facilitates electron transport. The electron transport material is one that can readily receive electrons from the cathode and transfer them to the light-emitting layer; materials with high electron mobility are suitable. Examples of suitable electron transport materials include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, and hydroxyflavonoid-metal complexes, but these are not limited to these. The thickness of the electron transport layer can range from 1 to 50 nm. A thickness of 1 nm or more has the advantage of preventing a decrease in electron transport properties, while a thickness of less than 50 nm has the advantage of preventing an increase in driving voltage to improve electron migration when the electron transport layer is too thick.

[0308] The aforementioned electron injection layer facilitates electron injection. Preferred electron injection materials include compounds that possess electron transport capabilities, effectively inject electrons from the cathode, exhibit excellent electron injection performance for the light-emitting layer or material, prevent excitons generated in the light-emitting layer from migrating to the hole injection layer, and demonstrate excellent thin-film formation ability. Examples of such electron injection materials include fluorenone, anthraquinone dimethyl ether, biphenylquinone, and thiamethoxam dioxide. azole, Diazoles, triazoles, triazines, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0309] The aforementioned electron transport layer and electron injection layer can be formed as a single layer. For example, the electron injection material and the electron transport material can be vacuum-deposited simultaneously, or a material that exhibits both electron injection and transport effects can be vacuum-deposited to form an electron injection and transport layer.

[0310] The aforementioned electron injection and transport layer may also contain metal ligands. Examples of such metal ligands include 8-hydroxyquinoline Al complexes (Alq3), LiQ, and metal coordination compounds, but are not limited to these. For example, triazine derivatives and lithium quinoline (LiQ) can be used in the aforementioned electron injection and transport layer, but are not limited to these.

[0311] 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.

[0312] In one embodiment of this specification, the electron injection and transport layer comprises a compound represented by the following chemical formula ET-1, but is not limited thereto.

[0313] [Chemical formula ET-1]

[0314]

[0315] In the above chemical formula ET-1,

[0316] At least one of Z11 to Z13 is N, and the rest are CH.

[0317] At least one of Z21 to Z23 is N, and the rest are CH.

[0318] L601 and L602 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

[0319] Ar601 to Ar604 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 heteroaryl group.

[0320] In one embodiment of this specification, L601 and L602 may be the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0321] In one embodiment of this specification, L601 and L602 are phenylene oxides.

[0322] In one embodiment of this specification, Ar601 to Ar604 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0323] In one embodiment of this specification, Ar601 to Ar604 are phenyl groups.

[0324] In one embodiment of this specification, the above chemical formula ET-1 is represented by the following compound.

[0325]

[0326] In one embodiment of this specification, the electron injection and transport layer may further comprise a metal coordination compound. The metal coordination compound is as described above.

[0327] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0328] Furthermore, 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.

[0329] The following examples will be provided to illustrate this specification in detail. However, the embodiments described in this specification can be modified in various ways and should not be construed as limiting the scope of this application to the embodiments detailed below. The embodiments of this application are provided to provide a more complete explanation of this specification to those skilled in the art.

[0330] <Manufacturing Example>

[0331] Manufacturing Example 1: Synthesis of Compound 1

[0332]

[0333] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, bromobenzene (3.50 g, 22.29 mmol) and compound a-1 (8.02 g, 18.95 mmol) were completely dissolved in 250 mL of xylene. Sodium tert-butoxide (NaOtBu) (3.21 g, 33.44 mmol) and bis(tri-tert-butylphosphine)palladium(O)(BTP) (0.11 g, 0.22 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was then recrystallized from 290 mL of ethyl acetate to prepare compound 1 (6.54 g, 59%).

[0334] MS[M+H] + =499

[0335] Manufacturing Example 2: Synthesis of Compound 2

[0336]

[0337] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, bromobenzene (3.50 g, 22.29 mmol) and compound a-2 (8.02 g, 18.95 mmol) were completely dissolved in 250 mL of xylene. NaOtBu (3.21 g, 33.44 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.11 g, 0.22 mmol). The mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure. The solution was recrystallized from 270 mL of ethyl acetate to prepare compound 2 (6.11 g, 55%). MS [M+H] + =499

[0338] Manufacturing Example 3. Synthesis of Compound 3

[0339]

[0340] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, bromobenzene (3.50 g, 22.29 mmol) and compound a-3 (9.42 g, 18.95 mmol) were completely dissolved in 240 mL of xylene. NaOtBu (3.21 g, 33.44 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.11 g, 0.22 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure. The solution was recrystallized from 300 mL of ethyl acetate to prepare compound 3 (7.23 g, 57%). MS [M+H] + =574

[0341] Manufacturing Example 4. Synthesis of Compound 4

[0342]

[0343] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 3-bromo-1,1'-biphenyl-2,2',3',4,4',5,5',6,6'-d9 (3-bromo-1,1'-biphenyl-2,2',3',4,4',5,5',6,6'-d9) (3.50 g, 14.46 mmol) and compound a-4 (5.26 g, 12.29 mmol) were completely dissolved in 260 mL of xylene. NaOtBu (2.08 g, 21.69 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.07 g, 0.14 mmol) were added, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure. The solution was recrystallized from 240 mL of ethyl acetate to prepare compound 4 (5.53 g, 65%). MS [M+H] + =589

[0344] Manufacturing Example 5. Synthesis of Compound 5

[0345]

[0346] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 5'-bromo-1,1':3',1”-terphenyl (3.50 g, 11.33 mmol) and compound a-5 (4.07 g, 9.63 mmol) were completely dissolved in 240 mL of xylene. NaOtBu (1.63 g, 16.99 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.06 g, 0.11 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure. The solution was recrystallized from 280 mL of ethyl acetate to prepare compound 5 (4.89 g, 66%). MS [M+H] + =651

[0347] Manufacturing Example 6. Synthesis of Compound 6

[0348]

[0349] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 3-bromo-1,1':3',1”-terphenyl-2,2',2”,3”,4,4',4”,5,5',5”,6,6',6”-d13(3-bromo-1,1':3',1”-terphenyl-2,2',2”,3”,4,4',4”,5,5',5”,6,6',6”-d13) (3.50 g, 6.69 mmol) and compound a-4 (3.01 g, 7.02 mmol) were completely dissolved in 260 mL of xylene. NaOtBu (1.29 g, 13.38 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.07 g, 0.13 mmol) were added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure. Recrystallization was then performed with 240 mL of ethyl acetate to produce compound 6 (3.91 g, 64%). MS[M+H] + =915 Manufacturing Example 7. Synthesis of Compound 7

[0350]

[0351] Under a nitrogen atmosphere, bromobenzene (3.50 g, 22.29 mmol) and compound a-6 (9.44 g, 18.95 mmol) were completely dissolved in 280 mL of xylene in a 500 mL round-bottom flask. NaOtBu (3.21 g, 33.44 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.11 g, 0.22 mmol). The mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The xylene was then concentrated under reduced pressure and recrystallized from 260 mL of ethyl acetate to prepare compound 7 (7.84 g, 61%). MS [M+H] + =575

[0352] Manufacturing Example 8. Synthesis of Compound 8

[0353]

[0354] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, 4-bromo-1,1'-biphenyl (3.50 g, 15.02 mmol) and compound a-7 (6.36 g, 12.77 mmol) were completely dissolved in 260 mL of xylene. NaOtBu (2.17 g, 22.53 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.08 g, 0.15 mmol) were added, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure. The solution was recrystallized from 290 mL of ethyl acetate to prepare compound 8 (6.75 g, 69%). MS [M+H] + =650

[0355] Manufacturing Example 9. Synthesis of Compound 9

[0356]

[0357] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, (3-bromophenyl)triphenylsilane (3.50 g, 8.43 mmol) and compound a-4 (3.06 g, 7.16 mmol) were completely dissolved in 250 mL of xylene. NaOtBu (1.21 g, 12.64 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.04 g, 0.08 mmol) were added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure. The solution was recrystallized from 270 mL of ethyl acetate to prepare compound 9 (4.77 g, 74%). MS [M+H] + =763

[0358] Manufacturing Example 10. Synthesis of Compound 10

[0359]

[0360] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound (3-bromophenyl-2,4,5,6-d4)tris(phenyl-d5)silane (3.50 g, 8.06 mmol) and compound a-4 (2.93 g, 6.85 mmol) were completely dissolved in 250 mL of xylene. NaOtBu (1.16 g, 12.10 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.04 g, 0.08 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 270 mL of ethyl acetate to prepare compound 10 (4.21 g, 67%). MS [M+H] + =782

[0361] Example 1-1.

[0362] ITO (indium tin oxide) is used in... A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. 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 process was repeated twice with distilled water for 10 minutes of ultrasonic washing. 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.

[0363] On the ITO transparent electrode prepared in this way as the anode, the following compounds HT1 and HI1 are formed by thermal vacuum evaporation in a ratio of 98:2. A hole injection layer of a certain thickness. The following compound HT1 is formed by vacuum evaporation onto the aforementioned hole injection layer. A hole transport layer of a certain thickness. Next, compound EB1 is vacuum-deposited onto the aforementioned hole transport layer to form... A thickness of electron blocking layer. Mixture A was prepared by mixing compound BH (n-type) and BH (p-type) synthesized in Manufacturing Example 1 at a weight ratio of 1:1. On the electron blocking layer, mixture A and compound BD were vacuum-deposited at a weight ratio of 88:12, thereby achieving a thickness of electron blocking layer. A light-emitting layer is formed on the thickness of the light-emitting layer. The following compound, BH(n-type), is then vacuum-deposited onto the light-emitting layer to form... A hole-blocking layer of thickness. Next, on the aforementioned hole-blocking layer, the following compounds ET1 and LiQ are vacuum-deposited in a 1:1 weight ratio, thereby achieving... The thickness forms an electron injection and transport layer. On this electron injection and transport layer, lithium fluoride (LiF) is sequentially applied... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness.

[0364]

[0365] During the above process, the evaporation rate of organic matter is maintained. to Lithium fluoride maintenance of the cathode The evaporation rate of aluminum maintains The evaporation rate is such that the vacuum level is maintained at 2 x 10 during evaporation. -7 Upgrade to 5x10 -6 This led to the creation of organic light-emitting devices.

[0366] Examples 1-2 to 1-10.

[0367] In Example 1-1 above, compound 1 was replaced by the compound listed in Table 1 below. Otherwise, the organic light-emitting device was manufactured by the same method as in Example 1-1 above.

[0368] Comparative Examples 1-1 to 1-4.

[0369] In Examples 1-1 above, compound 1 was replaced with the compounds listed in Table 1 below; otherwise, the organic light-emitting device was manufactured using the same method as in Examples 1-1 above. The following...

[0370] The C1 to C4 compounds used in Table 1 are shown below.

[0371]

[0372] Experimental example.

[0373] When an electric current was applied to the organic light-emitting devices manufactured in the above embodiments and comparative examples, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. 90 This refers to the time required for the brightness to decrease from the initial brightness (1600 nits) to 90%.

[0374] Table 1

[0375]

[0376] As shown in Table 1 above, the organic light-emitting devices of Examples 1-1 to 1-10, which use the compounds of the present invention as the p-type host of the hole transport region and the light-emitting layer, exhibit excellent characteristics in terms of efficiency, driving voltage and stability of organic light-emitting devices.

[0377] Conversely, when compounds C1 (Comparative Example 1-1) with R1 being a heteroaryl group; compounds C3 and C4 (Comparative Examples 1-3 and 1-4) with Ar1 being hydrogen or a heteroaryl group; and compounds C2 (Comparative Example 1-2) with both Ar1 and R1 being heteroaryl groups, the results showed increased voltage, decreased efficiency, and decreased stability (lifetime) compared to the organic light-emitting devices using compounds according to Formula 1 of this application.

[0378] The preferred embodiment (light-emitting layer) of the present invention has been described above, but the present invention is not limited thereto. Various modifications can be made within the scope of the claims and detailed description of the invention, and these modifications also fall within the scope of the present invention.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, L1 is a directly bonded, substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene. A is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted silyl group, or a substituted or unsubstituted heteroaryl group containing O or S. Ar1 is a substituted or unsubstituted aryl group. R1 to R3 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. R4 is either hydrogen or deuterium. r1 to r3 are each integers from 1 to 4, r4 is an integer from 1 to 3, and when r1 to r4 are 2 or more, the substituents in each parenthesis are the same or different from each other.

2. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] In the chemical formulas 1-1 to 1-3, L1, A, Ar1, R1 to R4 and r1 to r4 are the same as those defined in Chemical Formula 1.

3. The compound according to claim 1, wherein, The A is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted silyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

4. The compound according to claim 1, wherein, The Ar1 is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, or a substituted or unsubstituted naphthyl.

5. The compound according to claim 1, wherein, The R1 to R3 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, or substituted or unsubstituted aryl with 6 to 30 carbon atoms.

6. The compound according to claim 1, wherein, R1 to R3 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.

7. The compound according to claim 1, wherein, L1 is a directly bonded, deuterated or unsubstituted phenylene, or a deuterated or unsubstituted biphenylene.

8. The compound according to claim 1, wherein, The compound has any one of the following structures: In the structure described, Dn is the number of deuterium atoms contained in the compound.

9. An organic light-emitting device, wherein, include: anode, cathode, and One or more organic layers are disposed between the anode and the cathode. One or more of the organic layers comprise the compound described in any one of claims 1 to 8.

10. The organic light-emitting device according to claim 9, wherein, The organic layer includes a light-emitting layer. The luminescent layer contains the compound.

11. The organic light-emitting device according to claim 10, wherein, The light-emitting layer contains the compound as the main body of the light-emitting layer.

12. The organic light-emitting device according to claim 10, wherein, The light-emitting layer is a blue light-emitting layer.

13. The organic light-emitting device according to claim 10, wherein, The light-emitting layer also contains phosphorescent dopants.

14. The organic light-emitting device according to claim 9, wherein, The organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, wherein the hole injection layer, hole transport layer, or hole injection and transport layer contains the compound.

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