Compound and organic light-emitting element comprising same

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light-emitting element comprising same. The organic light-emitting element comprises: an anode; a cathode; and one or more organic material layers provided between the anode and the cathode, wherein one or more of the organic material layers comprise the compound.

Description

Compounds and organic light-emitting devices containing the same

[0001] The present application claims the benefit of the filing date of Korean Patent Application No. 10-2024-0181438 filed with the Korean Intellectual Property Office on December 9, 2024, the entire contents of which are incorporated herein.

[0002] This specification relates to a compound and an organic light-emitting device containing the same.

[0003] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) that utilize this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic layer. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton returns to the ground state.

[0004] The development of new materials for organic light-emitting devices as described above is continuously required.

[0005] The present specification provides a compound and an organic light-emitting device comprising the same.

[0006] One embodiment of the present specification provides a compound of the following chemical formula 1.

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

[0010] R1 is hydrogen; deuterium; or a substituted or unsubstituted aryl group, and

[0011] L1 is a substituted or unsubstituted arylene group, and

[0012] Ar1 is a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted pyridazine group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted pyrazol group; a substituted or unsubstituted furopyrimidine group; or a substituted or unsubstituted thienopyrimidine group, and

[0013] l1 is an integer from 1 to 5, and if l1 is 2 or greater, 2 or more L1s are the same or different from each other, and

[0014] r1 is an integer from 1 to 3, and if r1 is 2 or more, 2 or more R1s are the same or different from each other.

[0015] Another embodiment of the present specification provides an organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one of the organic layers comprises the compound.

[0016] A 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.

[0017] A compound according to a specific embodiment of the present invention can be used as a material for an electron injection layer, an electron transport layer, or an electron injection and transport layer of an organic light-emitting diode.

[0018] A compound according to one embodiment of the present invention can be incorporated into an organic light-emitting device to improve device characteristics, such as having a low driving voltage, excellent efficiency characteristics, or excellent lifespan characteristics.

[0019] FIGS. 1 to 3 illustrate organic light-emitting devices according to some embodiments of the present specification.

[0020] [Explanation of the symbol]

[0021] 1: Substrate

[0022] 2: Anode

[0023] 3: Organic layer

[0024] 4: Cathode

[0025] 5: Hole injection layer

[0026] 6: Precision Transport Layer

[0027] 6-1: 1st Precision Transport Layer

[0028] 6-2: Second Precision Transport Layer

[0029] 7: Emissive layer

[0030] 8: Electron injection and transport layer

[0031] The present specification will be described in more detail below.

[0032] The present specification provides a compound represented by the following chemical formula 1.

[0033] [Chemical Formula 1]

[0034]

[0035] In the above chemical formula 1,

[0036] R1 is hydrogen; deuterium; or a substituted or unsubstituted aryl group, and

[0037] L1 is a substituted or unsubstituted arylene group, and

[0038] Ar1 is a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted pyridazine group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted pyrazol group; a substituted or unsubstituted furopyrimidine group; or a substituted or unsubstituted thienopyrimidine group, and

[0039] l1 is an integer from 1 to 5, and if l1 is 2 or greater, 2 or more L1s are the same or different from each other, and

[0040] r1 is an integer from 1 to 3, and if r1 is 2 or more, 2 or more R1s are the same or different from each other.

[0041] The compound represented by Chemical Formula 1 of the present invention can effectively control electron mobility by including a thiophene unit. Therefore, when applied to an organic light-emitting diode, it can exhibit excellent efficiency and lifespan.

[0042] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0043] In this specification, when it is said that a member is located "on" another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members.

[0044] In the present specification, the meaning of a specific A substance being included in a B layer includes both i) one or more types of A substances being included in a single B layer and ii) the B layer being composed of one or more layers and A substance being included in one or more layers among the multilayer B layers.

[0045] In the present specification, the meaning that a specific A substance is included in a C layer or a D layer is that i) the A substance is included in one or more of the C layers, ii) the A substance is included in one or more of the D layers, or iii) the A substance is included in one or more of the C layers and one or more of the D layers, respectively.

[0046] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, the site where the substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0047] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; cyano group (-CN); nitro group; hydroxyl group; alkyl group; cycloalkyl group; alkoxy group; phosphine oxide group; aryloxy group; alkylthioxy group; arylthioxy group; alkyl sulfoxy group; aryl sulfoxy group; alkenyl group; silyl group; boron group; amine group; aryl group; and heterocyclic group, or is substituted with a substituent in which two or more of the exemplified substituents are connected, or has no substituents. For example, “a substituent in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

[0048] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; cyano group; silyl group; alkoxy group; aryloxy group; alkyl group; aryl group; and heterocyclic group, or that it is substituted with a substituent in which two or more of the exemplified substituents are connected, or that it has no substituents.

[0049] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen groups; cyano groups; alkyl groups; aryl groups; and heterocyclic groups, or that it is substituted with two or more of the exemplified substituents linked together, or that it has no substituents.

[0050] In this specification, the term “substituted or unsubstituted with one or more selected from the group consisting of A, B, and C” means that it is substituted with one or two or more substituents selected from the group consisting of listed substituents (A, B, and C), or is substituted with a substituent in which two or more of the listed substituents are connected, or has no substituents at all. For example, “an arylene group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano group, and aryl group” includes an arylene group substituted with deuterium, an arylene group substituted with a cyano group, and an arylene group substituted with an aryl group, as well as an arylene group substituted with a deuterium-substituted aryl group.

[0051] Examples of the above substituents are described below, but are not limited thereto.

[0052] In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0053] In this specification, the silyl group may be represented by the chemical formula -SiYaYbYc, wherein Ya, Yb, and Yc may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specifically, the silyl group may be a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a biphenyldiphenylsilyl group, a phenylsilyl group, etc., but is not limited thereto. The number of carbon atoms in the silyl group may be 3 to 60, but is not limited thereto.

[0054] In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. In one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. In another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. In yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of alkyl groups include, butyl, n-butyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0055] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

[0056] Substituents comprising alkyl groups, alkoxy groups and other alkyl groups described in this specification include both straight-chain and broken-chain forms.

[0057] In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. In one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. In another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. In yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. 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, stilbenyl group, styrenyl group, etc., but are not limited to these.

[0058] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and in one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. In another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. In yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, etc., are included, but are not limited thereto.

[0059] In the present specification, the amine group is -NH2, and the amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms in the substituted amine group is not particularly limited, but is preferably 1 to 30. In one embodiment, the number of carbon atoms in the amine group is 1 to 20. In one embodiment, the number of carbon atoms in the amine group is 1 to 10. Specific examples of substituted amine groups include, but are not limited to, methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, 9,9-dimethylfluorenylphenylamine, pyridylphenylamine, diphenylamine, phenylpyridylamine, naphthylamine, biphenylamine, anthracenylamine, dibenzofuranylphenylamine, 9-methylanthracenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, and diphenylamine groups.

[0060] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. In one embodiment, the number of carbon atoms of the aryl group is 6 to 30. In one embodiment, the number of carbon atoms of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quadrphenyl group, etc., but is not limited thereto. As a polycyclic aryl group, the aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto.

[0061] In the present specification, the fluorenyl group may be substituted, and two substituents may combine to form a spiro structure.

[0062] When the above fluorenyl group is substituted, , Spirofluorenyl group of the back, etc. (9,9-dimethylfluorenyl group), and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited to this.

[0063] In this specification, an arylene group refers to a group having two bonding sites to an aryl group, i.e., a divalent group. Except for being divalent, the description of arylene groups described above may apply. For example, a phenylene group is a divalent phenyl group.

[0064] In this specification, the aryl group among the aryloxy groups may be subject to the description of the aryl group described above.

[0065] In the present specification, the heterocyclic group is a ring group comprising one or more of the heteroatoms N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. In one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. In one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of heterocyclic groups include pyridine, pyrrole, pyrimidine, quinoline, pyridazine, furan, thiophene, imidazole, pyrazol, dibenzofuran, dibenzothiophen, carbazole, benzocarbazole, naphthobenzofuran, benzonaphthothiophen, indenocarbazole, pyridazine, benzimidazole, furopyrimidine, thienopyrimidine, and triazine, but are not limited to these.

[0066] Unless otherwise defined in this specification, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present invention pertains. Methods and materials similar or equivalent to those described herein may be used in the practice or testing of embodiments of the present invention, but suitable methods and materials are described below. 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 not mentioned, this specification, including definitions, shall prevail. Furthermore, materials, methods, and embodiments are merely illustrative and are not intended to be limiting.

[0067] The compound of Chemical Formula 1 above will be described in detail below.

[0068] In one embodiment of the present specification, the formula 1 is the following formula 1-1 or 1-2.

[0069] [Chemical Formula 1-1]

[0070]

[0071] [Chemical Formula 1-2]

[0072]

[0073] In the above chemical formulas 1-1 and 1-2,

[0074] R1, R1' and R1'' are the same or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted aryl group, and

[0075] L1 is a substituted or unsubstituted arylene group, and

[0076] Ar1 is a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted pyridazine group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted pyrazol group; a substituted or unsubstituted furopyrimidine group; or a substituted or unsubstituted thienopyrimidine group, and

[0077] l1 is an integer from 1 to 5, and if l1 is 2 or more, 2 or more L1s are the same or different from each other.

[0078] In one embodiment of the present specification, the formula 1 is the formula 1-1.

[0079] In one embodiment of the present specification, the formula 1 is the formula 1-2.

[0080] In one embodiment of the present specification, R1 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0081] In one embodiment of the present specification, R1 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

[0082] In one embodiment of the present specification, r1 is 3.

[0083] In one embodiment of the present specification, L1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0084] In one embodiment of the present specification, L1 is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted divalent anthracene group.

[0085] In one embodiment of the present specification, L1 is an arylene group substituted or unsubstituted with one or more types selected from the group consisting of deuterium, cyano groups and aryl groups.

[0086] In one embodiment of the present specification, L1 is a phenylene group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups and aryl groups; a biphenylene group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups and aryl groups; a terphenylene group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups and aryl groups; a naphthylene group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups and aryl groups; or a divalent anthracene group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups and aryl groups.

[0087] In one embodiment of the present specification, Ar1 is any one of the following structures.

[0088]

[0089]

[0090] In the above structure,

[0091] R10 to R33 are the same or different from one another, and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and

[0092] r15 is 1 or 2, r10, r13, r14 and r23 are each integers from 1 to 3, r18 and r20 are each integers from 1 to 4, and if r10, r13, r14, r15, r18, r20 and r23 are 2 or more, the substituents in each parenthesis are the same or different from each other.

[0093] In one embodiment of the present specification, R10 to R33 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0094] In one embodiment of the present specification, R10 to R33 are the same or different from each other and are each independently an alkyl group substituted or unsubstituted with one or more selected from the group consisting of hydrogen; deuterium; deuterium, cyano group, aryl group and heterocyclic group; or an aryl group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano group, aryl group and heterocyclic group.

[0095] In one embodiment of the present specification, R10 to R33 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl 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 fluorene group; or a substituted or unsubstituted phenanthrene group.

[0096] In one embodiment of the present specification, R10 to R33 are the same or different from each other and each independently comprises: hydrogen; deuterium; a methyl group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups, aryl groups, and heterocyclic groups; an ethyl group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups, aryl groups, and heterocyclic groups; a propyl group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups, aryl groups, and heterocyclic groups; a butyl group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups, aryl groups, and heterocyclic groups; and a phenyl group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups, aryl groups, and heterocyclic groups. A biphenyl group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups, aryl groups, and heterocyclic groups; a terphenyl group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups, aryl groups, and heterocyclic groups; a naphthyl group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups, aryl groups, and heterocyclic groups; a fluorene group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups, aryl groups, and heterocyclic groups; or a phenanthrene group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups, aryl groups, and heterocyclic groups.

[0097] In one embodiment of the present specification, the compound is any one of the following structures.

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] The substituents of the compound of Chemical Formula 1 above may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[0109] The following describes organic light-emitting diodes in detail.

[0110] One embodiment of the present specification provides an organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprise the compound.

[0111] The organic light-emitting device of the present invention can be manufactured by conventional methods and materials for manufacturing organic light-emitting devices, except that one or more organic layers are formed using the aforementioned compound.

[0112] The above compound can be formed as an organic layer by vacuum deposition as well as by solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0113] For example, the organic light-emitting diode of the present specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, the device can be manufactured by using a physical vapor deposition (PVD) method, such as sputtering or electron beam evaporation, to form an anode by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate, forming an organic layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting diode can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0114] In one embodiment of the present specification, the organic layer may be formed as a single layer structure, or it may be formed as a multilayer structure in which two or more organic layers are stacked. For example, when the organic light-emitting device comprises a plurality of organic layers, the organic layer may 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, a hole blocking 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 thereto and may include a smaller or larger number of organic layers.

[0115] The above organic layer may be formed from the same material or a different material. Additionally, the above organic layer may be formed using various polymer materials by deposition and / or solution processes.

[0116] In one embodiment of the present specification, the organic layer includes a light-emitting layer. In this case, the light-emitting layer may or may not include the compound of Formula 1.

[0117] In one embodiment of the present specification, the organic layer comprises a light-emitting layer and further comprises one or more organic layers in addition to the light-emitting layer.

[0118] In one embodiment of the present specification, the organic light-emitting element comprises an anode; a cathode; and a light-emitting layer provided between the anode and the cathode, and further comprises a multilayer organic layer between the light-emitting layer and the cathode, wherein one or more of the organic layers comprise a compound of Formula 1.

[0119] In one embodiment of the present specification, the organic layer on the side closer to the light-emitting layer among the multilayer organic layers comprises the compound.

[0120] In one embodiment of the present specification, the organic light-emitting element comprises an anode; a cathode; and a light-emitting layer provided between the anode and the cathode, and further comprises a single layer of organic material between the light-emitting layer and the cathode, wherein the organic material layer comprises a compound of Formula 1.

[0121] In one embodiment of the present specification, the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, electron transport layer, or electron injection and transport layer comprises the compound.

[0122] In one embodiment of the present specification, the electron injection layer, the electron transport layer, or the electron injection and transport layer further comprises a metal complex.

[0123] In one embodiment of the present specification, the electron injection and transport layer further comprises a metal complex.

[0124] In one embodiment of the present specification, the organic layer comprises a hole blocking layer, and the hole blocking layer comprises the compound.

[0125] In one embodiment of the present specification, the organic layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0126] In one embodiment of the present specification, the organic light-emitting element comprises an anode; a cathode; and a light-emitting layer provided between the anode and the cathode, and further comprises one or more layers among a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer between the light-emitting layer and the cathode, wherein one or more layers among the hole blocking layer, the electron injection layer, the electron transport layer, and the electron injection and transport layer comprise the compound.

[0127] In one embodiment of the present specification, an additional organic layer may be further included between the light-emitting layer and the anode. For example, one or more layers among an electron blocking layer, a hole injection layer, a hole transport layer, and a hole injection and transport layer may be further included between the light-emitting layer and the anode. In this case, the additional organic layer may or may not include the compound of Formula 1.

[0128] For example, the structure of the organic light-emitting element of the present specification may have a structure such as that shown in FIGS. 1 to 3, but is not limited thereto.

[0129] FIG. 1 illustrates the structure of an organic light-emitting device in which an anode (2), an organic layer (3), and a cathode (4) are sequentially stacked on a substrate (1). FIG. 1 is an exemplary structure of an organic light-emitting device according to one embodiment of the present specification and may further include other organic layers.

[0130] FIG. 2 illustrates the structure of an organic light-emitting device in which an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (7), an electron injection and transport layer (8), and a cathode (4) are sequentially stacked on a substrate (1). FIG. 2 is an exemplary structure according to an embodiment of the present specification and may further include other organic layers.

[0131] FIG. 3 illustrates the structure of an organic light-emitting device in which an anode (2), a hole injection layer (5), a first hole transport layer (6-1), a second hole transport layer (6-2), a light-emitting layer (7), an electron injection and transport layer (8), and a cathode (4) are sequentially stacked on a substrate (1). FIG. 3 is an exemplary structure according to an embodiment of the present specification and may further include other organic layers.

[0132] Specifically, the organic light-emitting device may have a stacked structure such as the following, in addition to the structure specified in the drawing, but is not limited thereto.

[0133] (1) Anode / hole transport layer / emissive layer / cathode

[0134] (2) Anode / hole injection layer / hole transport layer / emissive layer / cathode

[0135] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / cathode

[0136] (4) Anode / hole transport layer / emissive layer / electron transport layer / cathode

[0137] (5) Anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0138] (6) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / cathode

[0139] (7) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0140] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / cathode

[0141] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0142] (10) Anode / Hole transport layer / Electron blocking layer / Emitting layer / Electron transport layer / Cathode

[0143] (11) Anode / hole transport layer / electron blocking layer / emissive layer / electron transport layer / electron injection layer / cathode

[0144] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / emissive layer / electron transport layer / cathode

[0145] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / emissive layer / electron transport layer / electron injection layer / cathode

[0146] (14) Anode / hole transport layer / emissive layer / hole blocking layer / electron transport layer / cathode

[0147] (15) Anode / hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0148] (16) Anode / hole injection layer / hole transport layer / emissive layer / hole blocking layer / electron transport layer / cathode

[0149] (17) Anode / hole injection layer / hole transport layer / emissive layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0150] (18) Anode / hole injection layer / hole transport layer / electron blocking layer / emissive layer / hole blocking layer / electron injection and transport layer / cathode

[0151] (19) Anode / hole injection layer / hole transport layer / emissive layer / electron injection and transport layer / cathode

[0152] (20) Anode / hole injection layer / first hole transport layer / second hole transport layer / emissive layer / electron injection and transport layer / cathode

[0153] In one embodiment of the present specification, the 'electron transport layer / electron injection layer' may be replaced with an 'electron injection and transport layer' or a 'layer that performs electron injection and transport simultaneously'.

[0154] In one embodiment of the present specification, the 'hole injection layer / hole transport layer' may be replaced with a 'hole injection and transport layer' or a 'layer that performs hole injection and transport simultaneously'.

[0155] The above anode is an electrode that injects holes, and as the anode material, it is generally preferable to use an organic layer with a high work function to facilitate hole injection. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; 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-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0156] The above cathode is an electrode for injecting electrons, and the cathode material is typically an organic layer, preferably a material with a low work function to facilitate electron injection. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0157] The hole injection layer described above is a layer that facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is a material capable of receiving holes well from the anode at low voltage, and 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 metal porphyrine, oligothiophene, arylamine-based organic materials, heteroarylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers of polyaniline and polythiophene series, but are not limited to these. For example, the hole injection material may be a compound containing substituted or unsubstituted acridine, but is not limited to this.

[0158] In one embodiment of the present specification, the thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, there is an advantage of preventing the driving voltage from rising to improve the movement of holes due to the thickness of the hole injection layer being too thick.

[0159] In one embodiment of the present specification, the hole injection layer comprises a compound represented by the following chemical formula HI-1.

[0160] [Chemical Formula HI-1]

[0161]

[0162] In the above chemical formula HI-1,

[0163] R401 to R405 are the same or different from each other, and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring, and

[0164] R406 is hydrogen; deuterium; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, and

[0165] R406 is an integer from 1 to 8, and if r406 is 2 or more, 2 or more R406s are the same or different from each other.

[0166] In one embodiment of the present specification, R401 is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or is combined with adjacent groups to form a substituted or unsubstituted ring.

[0167] In one embodiment of the present specification, R401 is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0168] In one embodiment of the present specification, R401 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0169] In one embodiment of the present specification, R401 is a substituted or unsubstituted aryl group.

[0170] In one embodiment of the present specification, R401 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0171] In one embodiment of the present specification, R401 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0172] In one embodiment of the present specification, R401 is a substituted or unsubstituted phenyl group.

[0173] In one embodiment of the present specification, R402 to R405 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0174] In one embodiment of the present specification, R402 to R405 are the same or different from one another and are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0175] In one embodiment of the present specification, R402 to R405 are the same or different from one another and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heterocyclic groups.

[0176] In one embodiment of the present specification, R402 to R405 are the same or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms; or substituted or unsubstituted heterocyclic groups having 2 to 30 carbon atoms.

[0177] In one embodiment of the present specification, R402 and R404 are the same or different from each other and are each independently substituted or unsubstituted aryl groups.

[0178] In one embodiment of the present specification, R402 and R404 are the same or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0179] In one embodiment of the present specification, R402 and R404 are the same or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

[0180] In one embodiment of the present specification, R402 and R404 are the same or different from each other and are each independently substituted or unsubstituted phenyl groups.

[0181] In one embodiment of the present specification, R403 and R405 are the same or different from each other and are each independently substituted or unsubstituted heterocyclic rings.

[0182] In one embodiment of the present specification, R403 and R405 are the same or different from each other and are each independently substituted or unsubstituted heterocyclic rings having 2 to 30 carbon atoms.

[0183] In one embodiment of the present specification, R403 and R405 are the same or different from each other and are each independently substituted or unsubstituted heterocyclic rings having 2 to 20 carbon atoms.

[0184] In one embodiment of the present specification, R403 and R405 are the same or different from each other and are each independently a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophen group or a substituted or unsubstituted carbazole group.

[0185] In one embodiment of the present specification, R403 and R405 are the same or different from each other and are each independently substituted or unsubstituted carbazole groups with aryl groups.

[0186] In one embodiment of the present specification, R403 and R405 are the same or different from each other and are each independently a carbazole group substituted or unsubstituted with a phenyl group.

[0187] In one embodiment of the present specification, R406 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0188] In one embodiment of the present specification, R406 is hydrogen; or deuterium.

[0189] In one embodiment of the present specification, the formula HI-1 comprises the following compound.

[0190]

[0191] The hole transport layer described above can facilitate the transport of holes. As a hole transport material, a material capable of receiving holes from an anode or a hole injection layer and transferring them to an emissive layer is suitable if it has high mobility for holes. Specific examples include arylamine-based organic materials, heteroarylamine-based organic materials, carbazole-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these. For example, the hole transport material may be one or more of a compound containing substituted or unsubstituted quinoxaline and a compound containing a substituted or unsubstituted amine group, but is not limited to these.

[0192] In one embodiment of the present specification, the hole transport layer comprises a compound of the following formula HT-1.

[0193] [Chemical Formula HT-1]

[0194]

[0195] In the above chemical formula HT-1,

[0196] At least one of X'1 to X'6 is N, and the rest are CH, and

[0197] R309 to R314 are the same or different from each other and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0198] In one embodiment of the present specification, X'1 to X'6 are N.

[0199] In one embodiment of the present specification, R309 to R314 are cyano groups.

[0200] In one embodiment of the present specification, the formula HT-1 comprises the following compound.

[0201]

[0202] In one embodiment of the present specification, the hole transport layer comprises a compound represented by the following chemical formula HT-2.

[0203] [Chemical Formula HT-2]

[0204]

[0205] In the above chemical formula HT-2,

[0206] R315 to R317 are the same or different from one another and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; and combinations thereof, or are bonded to adjacent groups to form a substituted or unsubstituted ring, and

[0207] r315 is an integer from 1 to 5, and if r315 is 2 or more, the 2 or more R315s are the same or different from each other,

[0208] r316 is an integer from 1 to 5, and if r316 is 2 or more, the 2 or more R316s are the same or different from each other.

[0209] In one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; and combinations thereof.

[0210] In one embodiment of the present specification, the R317 is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted fluorene group, or adjacent groups are combined to form a substituted or unsubstituted ring group.

[0211] In one embodiment of the present specification, R317 is a substituted or unsubstituted fluorene group.

[0212] In one embodiment of the present specification, R315 and R316 are the same or different from each other and are each independently hydrogen; deuterium; or substituted or unsubstituted heterocyclic rings.

[0213] In one embodiment of the present specification, R315 and R316 are the same or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted carbazole group.

[0214] In one embodiment of the present specification, the chemical formula HT-2 is any one of the following structures.

[0215]

[0216] In one embodiment of the present specification, the hole transport layer may include one or more of the compound of formula HT-1 and the compound of formula HT-2.

[0217] In one embodiment of the present specification, the hole transport layer comprises a compound of formula HT-1 and a compound of formula HT-2.

[0218] In one embodiment of the present specification, the hole transport layer may be composed of a first hole transport layer and a second hole transport layer.

[0219] According to one embodiment of the present specification, the first hole transport layer may include a compound of the formula HT-1.

[0220] According to one embodiment of the present specification, the second hole transport layer may include a compound of the formula HT-2.

[0221] The above-mentioned light-emitting layer may emit red, green, or blue light and may be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole, and benzimidazole series; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0222] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0223] In one embodiment of the present specification, the host comprises a compound of the following formula H-1.

[0224] [Chemical Formula H-1]

[0225]

[0226] In the above chemical formula H-1,

[0227] L20 and L21 are the same or different from each other, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group, and

[0228] Ar20 and Ar21 are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0229] R2O1 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0230] r201 is an integer from 1 to 8, and if r201 is 2 or more, the 2 or more R201s are the same or different from each other.

[0231] In one embodiment of the present specification, L20 and L21 are the same or different from each other and are each independently directly bonded; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0232] In one embodiment of the present specification, L20 and L21 are the same or different from each other and are each independently direct bonded; a phenylene group substituted or unsubstituted with deuterium; a biphenyllylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a dibenzofuran group; or a dibenzothiophene group.

[0233] In one embodiment of the present specification, L20 and L21 are each direct couplings.

[0234] In one embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; or substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms.

[0235] In one embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 20 carbon atoms and 4 rings; or substituted or unsubstituted heterocyclic groups having 6 to 20 carbon atoms and 4 rings.

[0236] In one embodiment of the present specification, the Ar20 and Ar21 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted dibenzothiophen group; or a naphthobenzothiophen group.

[0237] In one embodiment of the present specification, the Ar20 and Ar21 are the same or different from each other and are each independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a thiophene group substituted or unsubstituted with one or more selected from the group consisting of deuterium and phenyl groups; a phenanthrene group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a naphthobenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophene group substituted or unsubstituted with deuterium; or a naphthobenzothiophene group substituted or unsubstituted with deuterium.

[0238] In one embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and are each independently a phenyl group or a naphthyl group.

[0239] According to one embodiment of the present specification, R201 is hydrogen; deuterium; a phenyl group; or a naphthyl group.

[0240] According to one embodiment of the present specification, the chemical formula H-1 is any one of the following structures.

[0241]

[0242] When the emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the light-emitting layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distrylarylene (DSA), PFO-based polymers, and PPV-based polymers may be used as light-emitting dopants, but are not limited to these.

[0243] In one embodiment of the present specification, the dopant comprises a compound of the following formula D-1.

[0244] [Chemical Formula D-1]

[0245]

[0246] In the above chemical formula D-1,

[0247] L501 and L502 are the same or different from each other, and are each independently directly bonded; or are substituted or unsubstituted arylene groups, and

[0248] R501 to R504 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0249] In one embodiment of the present specification, the formula D-1 is the following formula D-2.

[0250] [Chemical Formula D-2]

[0251]

[0252] In the above chemical formula D-2,

[0253] L501, L502, R501 to R504 are identical to those defined in the above chemical formula D-1.

[0254] In one embodiment of the present specification, L501 and L502 are each directly coupled.

[0255] In one embodiment of the present specification, R501 to R504 are the same or different from one another and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heterocyclic groups.

[0256] In one embodiment of the present specification, R501 to R504 are the same or different from one another and are each independently substituted or unsubstituted monocyclic aryl groups; or substituted or unsubstituted polycyclic aryl groups; or substituted or unsubstituted heterocyclic groups.

[0257] In one embodiment of the present specification, R501 to R504 are the same or different from one another and are each independently 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 anthracene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0258] In one embodiment of the present specification, R501 to R504 are the same or different from one another and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted dibenzofuran group.

[0259] In one embodiment of the present specification, R501 to R504 are the same or different from each other and are each independently a phenyl group substituted or unsubstituted with one or more selected from the group consisting of alkyl groups, silyl groups and aryl groups; or a terphenyl group substituted or unsubstituted with one or more selected from the group consisting of alkyl groups, silyl groups and aryl groups.

[0260] In one embodiment of the present specification, R501 to R504 are the same or different from one another and are each independently substituted or unsubstituted phenyl groups selected from the group consisting of methyl groups, tert-butyl groups, trimethylsilyl groups, and alkyl groups; or terphenyl groups substituted or unsubstituted from one or more selected from the group consisting of methyl groups, tert-butyl groups, and trimethylsilyl groups.

[0261] In one embodiment of the present specification, the chemical formulas D-1 and D-2 are each one of the following structures.

[0262]

[0263] The above electron transport layer can facilitate the transport of electrons. As an electron transport material, a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes, but are not limited to these.

[0264] In one embodiment of the present specification, the thickness of the electron transport layer may be 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, there is an advantage of preventing the driving voltage from rising to improve electron movement because the thickness of the electron transport layer is too thick.

[0265] The electron injection layer described above can facilitate the injection of electrons. As an electron injection material, a compound is preferred that has the ability to transport electrons, has an excellent electron injection effect from the cathode, an excellent electron injection effect on the emissive layer or the emissive material, prevents the movement of excitons generated in the emissive layer to the hole injection layer, and also has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0266] In one embodiment of the present specification, the electron injection and transport layer can be manufactured by appropriately selecting the materials used for the electron injection layer and the electron transport layer.

[0267] In one embodiment of the present specification, the electron injection and transport layer may be manufactured using a compound of Formula 1.

[0268] In one embodiment of the present specification, the electron injection and transport layer comprises a compound of Formula 1 and a metal complex.

[0269] In one embodiment of the present specification, the electron injection and transport layer comprises the compound of Formula 1 and the metal complex in a weight ratio of 1:10 to 10:1.

[0270] In one embodiment of the present specification, the electron injection and transport layer comprises the compound of Formula 1 and the metal complex in a weight ratio of 1:3 to 3:1.

[0271] The above metal complex compounds include 8-hydroxyquinolinato lithium (Liq), bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, Examples include bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited thereto.

[0272] The hole blocking layer described above is a layer that prevents holes from reaching the cathode and can generally be formed under the same conditions as the hole injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc. are used, but are not limited thereto.

[0273] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0274] The organic light-emitting device of the present invention can be manufactured by conventional methods and materials for manufacturing organic light-emitting devices, except that one or more organic layers are formed using the aforementioned compound.

[0275] The organic light-emitting element according to the present invention may be included in various electronic devices. For example, an electronic device including the organic light-emitting element may be a light-emitting device, an authentication device, a display device, a lighting device, a mobile terminal, a wearable device, and various other electronic devices. Specifically, the display device may include a TV, a monitor, a smartphone, a tablet, a laptop display, a smartwatch, a vehicle cluster, a VR / AR display, lighting, etc.

[0276] Hereinafter, to specifically explain this specification, examples will be described in detail. However, the embodiments according to this specification may be modified in various different forms, and the scope of this specification is not to be interpreted as being limited to the embodiments described below. The embodiments of this specification are provided to more completely explain this specification to those with average knowledge in the art.

[0277] Preparation Example 1. Preparation of Compound E1

[0278]

[0279] E1-A (20 g, 51.1 mmol) and E1-B (31.5 g, 53.7 mmol) were added to 400 ml of 1,4-Dioxane under a nitrogen atmosphere and stirred and refluxed. Subsequently, tripotassium phosphate (32.6 g, 153.3 mmol) was dissolved in 150 ml of water and added, and after sufficient stirring, tetracitriphenyl-phosphinopalladium (0.37 g, 0.51 mmol) was added. After a reaction of 6 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 2000 ml of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was subjected to vacuum distillation. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare compound E1 (28.0 g, 70.9%).

[0280] MS: [M+H]+ = 772

[0281] Preparation Example 2. Preparation of Compound E2

[0282]

[0283] Compound E2 was prepared using the same method as the preparation method of Preparation Example 1, except that compound E2-B was used instead of compound E1-B in Preparation Example 1.

[0284] MS: [M+H]+ = 772

[0285] Preparation Example 3. Preparation of Compound E3

[0286]

[0287] Compound E3 was prepared using the same method as the preparation method of Preparation Example 1, except that E3-B was used instead of Compound E1-B in Preparation Example 1.

[0288] MS: [M+H]+ = 657

[0289] Preparation Example 4. Preparation of Compound E4

[0290]

[0291] Compound E4 was prepared using the same method as the preparation method of Preparation Example 1, except that E4-B was used instead of Compound E1-B in Preparation Example 1.

[0292] MS: [M+H]+ = 746

[0293] Preparation Example 5. Preparation of Compound E5

[0294]

[0295] Compound E5 was prepared using the same method as the preparation method of Preparation Example 1, except that compound E5-B was used instead of compound E1-B in Preparation Example 1.

[0296] MS: [M+H]+ = 695

[0297] Preparation Example 6. Preparation of Compound E6

[0298]

[0299] Compound E6 was prepared using the same method as the preparation method of Preparation Example 1, except that compound E6-B was used instead of compound E1-B in Preparation Example 1.

[0300] MS: [M+H]+ = 721

[0301] Preparation Example 7. Preparation of Compound E7

[0302]

[0303] Compound E7 was prepared using the same method as the preparation method of Preparation Example 1, except that compound E7-B was used instead of compound E1-B in Preparation Example 1.

[0304] MS: [M+H]+ = 797

[0305] Preparation Example 8. Preparation of Compound E8

[0306]

[0307] Compound E8 was prepared using the same method as the preparation method of Preparation Example 1, except that E8-A was used instead of Compound E1-A and E8-B was used instead of E1-B in Preparation Example 1.

[0308] MS: [M+H]+ = 649

[0309] Preparation Example 9. Preparation of Compound E9

[0310]

[0311] Compound E9 was prepared using the same method as the preparation method of Preparation Example 1, except that E9-A was used instead of Compound E1-A and E9-B was used instead of E1-B in Preparation Example 1.

[0312] MS: [M+H]+ = 821

[0313] Preparation Example 10. Preparation of Compound E10

[0314]

[0315] Compound E10 was prepared using the same method as the preparation method of Preparation Example 1, except that E10-A was used instead of compound E1-A and E10-B was used instead of E1-B in Preparation Example 1.

[0316] MS: [M+H]+ = 757

[0317] Preparation Example 11. Preparation of Compound E11

[0318]

[0319] Compound E11 was prepared using the same method as the preparation method of Preparation Example 1, except that E11-A was used instead of Compound E1-A and E11-B was used instead of E1-B in Preparation Example 1.

[0320] MS: [M+H]+ = 543

[0321] Preparation Example 12. Preparation of Compound E12

[0322]

[0323] Compound E12 was prepared using the same method as the preparation method of Preparation Example 1, except that E12-A was used instead of Compound E1-A and E12-B was used instead of E1-B in Preparation Example 1.

[0324] MS: [M+H]+ = 810

[0325] Preparation Example 13. Preparation of Compound E13

[0326]

[0327] Compound E13 was prepared using the same method as the preparation method of Preparation Example 1, except that E13-A was used instead of Compound E1-A and E13-B was used instead of E1-B in Preparation Example 1.

[0328] MS: [M+H]+ = 709

[0329] Preparation Example 14. Preparation of Compound E14

[0330]

[0331] Compound E14 was prepared using the same method as the preparation method of Preparation Example 1, except that E14-A was used instead of Compound E1-A and E14-B was used instead of E1-B in Preparation Example 1.

[0332] MS: [M+H]+ = 659

[0333] Preparation Example 15. Preparation of Compound E15

[0334]

[0335] Compound E15 was prepared using the same method as the preparation method of Preparation Example 1, except that E15-A was used instead of Compound E1-A and E15-B was used instead of E1-B in Preparation Example 1.

[0336] MS: [M+H]+ = 785

[0337] Preparation Example 16. Preparation of Compound E16

[0338]

[0339] Compound E16 was prepared using the same method as the preparation method of Preparation Example 1, except that E16-A was used instead of Compound E1-A and E16-B was used instead of E1-B in Preparation Example 1.

[0340] MS: [M+H]+ = 812

[0341] Preparation Example 17. Preparation of Compound E17

[0342]

[0343] Compound E17 was prepared using the same method as the preparation method of Preparation Example 1, except that E17-A was used instead of Compound E1-A and E17-B was used instead of E1-B in Preparation Example 1.

[0344] MS: [M+H]+ = 683

[0345] Preparation Example 18. Preparation of Compound E18

[0346]

[0347] Compound E18 was prepared using the same method as the preparation method of Preparation Example 1, except that E18-A was used instead of compound E1-A and E18-B was used instead of E1-B in Preparation Example 1.

[0348] MS: [M+H]+ = 751

[0349] Preparation Example 19. Preparation of Compound E19

[0350]

[0351] Compound E19 was prepared using the same method as the preparation method of Preparation Example 1, except that E19-A was used instead of Compound E1-A and E19-B was used instead of E1-B in Preparation Example 1.

[0352] MS: [M+H]+ = 649

[0353] Preparation Example 20. Preparation of Compound E20

[0354]

[0355] Compound E20 was prepared using the same method as the preparation method of Preparation Example 1, except that E20-A was used instead of Compound E1-A and E20-B was used instead of E1-B in Preparation Example 1.

[0356] MS: [M+H]+ = 699

[0357] Example 1.

[0358] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine. A hole injection layer was formed on the prepared ITO transparent electrode by thermal vacuum deposition of the following compound, HI-A, to a thickness of 600 Å. A hole transport layer was formed by sequentially vacuum depositing hexaazatriphenylene (HAT, 50 Å) of the following chemical formula and the following compound HT-A (600 Å) on the hole injection layer. Subsequently, a light-emitting layer was formed by vacuum depositing the following compounds BH and BD in a weight ratio of 25:1 on the hole transport layer to a film thickness of 200 Å. On the light-emitting layer, an electron injection and transport layer was formed to a thickness of 360 Å by vacuum depositing the compound E1 prepared in Example 1 and the following compound LiQ (Lithium quinolate) in a weight ratio of 1:1. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

[0359]

[0360] In the above process, the deposition rate of the organic material was maintained at 0.4 Å / sec to 0.9 Å / sec, while the deposition rates of lithium fluoride and aluminum for the cathode were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 5x10-8 torr to 1x10 -7 An organic light-emitting diode was fabricated by maintaining torr.

[0361] Examples 2 to 20.

[0362] An organic light-emitting diode was prepared in the same manner as in Example 1, except that the compound of Table 1 below was used instead of compound E1 in Example 1.

[0363] Comparative Examples 1 to 10.

[0364] An organic light-emitting diode was prepared in the same manner as in Example 1, except that the compounds in Table 1 below were used instead of compound E1 in Example 1. The compounds ET1 to ET10 used in Table 1 below are as follows.

[0365]

[0366] For the organic light-emitting devices prepared in Examples 1 to 20 and Comparative Examples 1 to 10 above, 10 mA / cm 2 The driving voltage, luminous efficiency, and color coordinates were measured at a current density of 20 mA / cm². 2 The time (T90) to reach 90% of the initial brightness at a current density was measured. The results are shown in Table 1 below.

[0367] Compound (electron injection and transport layer) voltage (V) (@10mA / cm²) 2 )Efficiency (cd / A)(@10mA / cm² 2 Color coordinates (x,y)T90 (hr)(@20mA / cm 2Example 1 E1 3.47 5.37 (0.144, 0.060) 276 Example 2 E2 3.60 5.15 (0.144, 0.061) 290 Example 3 E3 3.58 5.39 (0.144, 0.060) 307 Example 4 E4 3.49 5.32 (0.144, 0.061) 285 Example 5 E5 3.46 5.13 (0.144, 0.060) 268 Example 6 E6 3.50 5.42 (0.144, 0.060) 312 Example 7 E7 3.34 5.28 (0.145, 0.060) 274 8E83.415.38(0.144, 0.060)296 Example 9E93.455.50(0.144, 0.060)285 Example 10E103.395.48(0.144, 0.060)304 Example 11E113.665.33(0.144, 0.060)248 Example 12E123.245.46(0.144, 0.060)267 Example 13E133.705.81(0.144, 0.060)281 Example 14E143.816.10(0.144, 0.060)264 Example 15E153.545.77(0.144, 0.061)201 Example 16E163.945.64(0.144, 0.060)277 Example 17E173.485.28(0.144, 0.060)246 Example 18E183.575.19(0.144, 0.061)291 Example 19E193.455.64(0.144, 0.060)237 Example 20E203.665.37(0.144, 0.060)258 Comparative Example 1ET14.554.76(0.144, 0.060)194 Comparative Example 2ET24.224.25(0.144, 0.060)158 Comparative Example 3ET34.264.82(0.144, 0.060)167 Comparative Example 4ET44.854.65(0.144, 0.060)148 Comparative Example 5ET54.194.18(0.144, 0.060)112 Comparative Example 6ET64.664.76(0.144, 0.060)184 Comparative Example 7ET74.884.23(0.145, 0.060)142 Comparative Example 8ET84.184.95(0.144, 0.060)159 Comparative Example 9ET94.734.91(0.144, 0.060)134 Comparative Example 10ET104.544.88(0.144, 0.061)167

[0368] As described in Table 1 above, it can be confirmed that organic light-emitting devices (Examples 1 to 20) manufactured using the compound represented by Formula 1 of the present invention have a lower driving voltage and exhibit superior characteristics in efficiency and lifespan compared to organic light-emitting devices (Comparison 1 to 10) to which other compounds are applied.

Claims

1. Compound of Chemical Formula 1 below: [Chemical Formula 1] In the above chemical formula 1, R1 is hydrogen; deuterium; or a substituted or unsubstituted aryl group, and L1 is a substituted or unsubstituted arylene group, and Ar1 is a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted pyridazine group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted pyrazol group; a substituted or unsubstituted furopyrimidine group; or a substituted or unsubstituted thienopyrimidine group, and l1 is an integer from 1 to 5, and if l1 is 2 or greater, 2 or more L1s are the same or different from each other, and r1 is an integer from 1 to 3, and if r1 is 2 or more, 2 or more R1s are the same or different from each other.

2. A compound according to claim 1, wherein the chemical formula 1 is the following chemical formula 1-1 or 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In the above chemical formulas 1-1 and 1-2, R1, R1' and R1'' are the same or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted aryl group, and L1 is a substituted or unsubstituted arylene group, and Ar1 is a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted pyridazine group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted pyrazol group; a substituted or unsubstituted furopyrimidine group; or a substituted or unsubstituted thienopyrimidine group, and l1 is an integer from 1 to 5, and if l1 is 2 or more, 2 or more L1s are the same or different from each other.

3. A compound according to Claim 1, wherein Ar1 is one of the following structures: In the above structure, R10 to R33 are the same or different from one another, and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and r15 is 1 or 2, r10, r13, r14 and r23 are each integers from 1 to 3, r18 and r20 are each integers from 1 to 4, and if r10, r13, r14, r15, r18, r20 and r23 are 2 or more, the substituents in each parenthesis are the same or different from each other.

4. A compound according to claim 1, wherein R1 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

5. A compound according to claim 1, wherein L1 is an arylene group substituted or unsubstituted with one or more selected from the group consisting of deuterium, cyano groups and aryl groups.

6. A compound according to claim 1, wherein L1 is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted divalent anthracene group.

7. A compound according to Claim 1, wherein the chemical formula 1 is any one of the following structures: .

8. Anode; Cathode; and It includes one or more organic layers provided between the anode and the cathode, and An organic light-emitting device wherein one or more of the above organic layers comprise a compound of any one of claims 1 to 7.

9. An organic light-emitting device according to claim 8, wherein the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises the compound.

10. An organic light-emitting device according to claim 9, wherein the electron injection layer, the electron transport layer, or the electron injection and transport layer further comprises a metal complex.

11. An organic light-emitting device according to claim 8, wherein the organic layer comprises a hole-blocking layer, and the hole-blocking layer comprises the compound.

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