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.

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2023-0056397, filed with the Korean Patent Office on April 28, 2023, the entire contents of which are incorporated herein by reference.

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

[0003] Organic light-emitting devices (OLEDs) have a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to such an OLED, electrons and holes injected from the two electrodes recombine in the organic thin film, quench, and emit light. The organic thin film can be composed of a single layer or multiple layers, as needed.

[0004] As materials used in organic light-emitting devices, pure organic materials or coordination compounds of organic materials and metals constitute the majority. Depending on their application, they can be classified as hole injection materials, hole transport materials, luminescent materials, electron transport materials, and electron injection materials. Here, as hole injection or hole transport materials, organic materials with p-type properties are mainly used, i.e., organic compounds that are easily oxidized and have an electrochemically stable state when oxidized. On the other hand, as electron injection or electron transport materials, organic materials with n-type properties are mainly used, i.e., organic compounds that are easily reduced and have an electrochemically stable state when reduced. As the luminescent layer material, materials that simultaneously possess p-type and n-type properties are preferred, i.e., materials that have a stable form in both oxidized and reduced states. Preferably, materials with high luminescent efficiency are those that convert excitons generated by the recombination of holes and electrons in the luminescent layer into light.

[0005] To improve the performance, lifetime, or efficiency of organic light-emitting devices, there is a continuous demand for the development of organic thin film materials. Summary of the Invention

[0006] Technical issues

[0007] This specification provides compounds and organic light-emitting devices containing them.

[0008] Solution to the problem

[0009] One embodiment of this specification provides a compound of the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] L1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0014] L2 to L4 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0015] R1, R3, and R4 may be the same as or different from each other, and each can be hydrogen or deuterium independently.

[0016] R2 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0017] Ar1 and Ar2 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aromatic hydrocarbon rings with fused rings of aliphatic hydrocarbon rings, or substituted or unsubstituted heteroaryl.

[0018] r3 is an integer from 1 to 4. When r3 is 2 or higher, two or more R3 values ​​are the same or different from each other. r4 is an integer from 1 to 3. When r4 is 2 or higher, two or more R4 values ​​are the same or different from each other.

[0019] l2 and l3 are each integers from 1 to 3. When l2 is 2 or more, two or more L2s are the same or different from each other. When l3 is 2 or more, two or more L3s are the same or different from each other.

[0020] Another embodiment of this specification provides an organic light-emitting device, which includes: a first electrode, a second electrode, and one or more organic layers including a light-emitting layer disposed between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound of the above chemical formula 1.

[0021] Invention Effects

[0022] The compound according to one embodiment of this specification can be used as a material for the organic layer of an organic light-emitting device. By using the compound, it is possible to achieve improved efficiency, lower driving voltage, and / or improved lifetime characteristics in the organic light-emitting device.

[0023] In particular, when the compounds of the present invention are used in hole injection layers, hole transport layers or electron blocking layers, the effects of lower device drive voltage, increased device efficiency and longer device lifetime can be obtained. Attached Figure Description

[0024] Figure 1 and 2 The illustrations show organic light-emitting devices according to several embodiments of this specification.

[0025] 1: Substrate

[0026] 2: First electrode

[0027] 3: Emissive layer

[0028] 4: Second electrode

[0029] 5: Hole injection layer

[0030] 6: Hole transport layer

[0031] 7: Electron blocking layer

[0032] 8: Hole-blocking layer

[0033] 9: Electron Injection and Transport Layer Detailed Implementation

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

[0035] One embodiment of this specification provides a compound of the following chemical formula 1.

[0036] [Chemical Formula 1]

[0037]

[0038] In the above chemical formula 1,

[0039] L1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0040] L2 to L4 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0041] R1, R3, and R4 may be the same as or different from each other, and each can be hydrogen or deuterium independently.

[0042] R2 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0043] Ar1 and Ar2 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aromatic hydrocarbon rings with fused rings of aliphatic hydrocarbon rings, or substituted or unsubstituted heteroaryl.

[0044] r3 is an integer from 1 to 4. When r3 is 2 or higher, two or more R3 values ​​are the same or different from each other. r4 is an integer from 1 to 3. When r4 is 2 or higher, two or more R4 values ​​are the same or different from each other.

[0045] l2 and l3 are each integers from 1 to 3. When l2 is 2 or more, two or more L2s are the same or different from each other. When l3 is 2 or more, two or more L3s are the same or different from each other.

[0046] According to one embodiment of this specification, the compound is represented by Chemical Formula 1 as described above. When indicating the carbon numbering of the phenanthrene group as follows, the compound of Chemical Formula 1 contains specific substituents at positions 2 and 10 of the phenanthrene group. Therefore, when applied to organic light-emitting devices, it can exhibit effects such as low voltage, high efficiency, and / or long lifetime.

[0047]

[0048] 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.

[0049] 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.

[0050] In this specification, the term "layer" is used interchangeably with "film" primarily used in this technical field, referring to a coating covering a target area. The size of the "layer" is not limited; the sizes of individual "layers" can be the same or different. In one embodiment, the size of a "layer" can be equal to the size of the entire device, equivalent to the size of a specific functional area, or as small as a single subpixel.

[0051] In this specification, "or" means inclusive rather than exclusive. For example, condition A or B means that any of the following conditions are met: A is true (or exists), B is false (or does not exist); A is false (or does not exist), B is true (or exists); and both A and B are true (or exist).

[0052] In this specification, the meaning of a specific substance A being contained in layer B includes both i) cases where one or more substances A are contained in a single layer of layer B and ii) cases 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.

[0053] In this specification, the meaning of a specific substance A being contained in layer C or layer D is all of the following: substance A i) is contained in one or more layers of layer C, or ii) is contained in one or more layers of layer D, or iii) is contained in one or more layers of layer C and one or more layers of layer D respectively.

[0054] In this specification, "---" indicates the site where it connects with other substituents or binding sites.

[0055] Examples of substituents in this specification are described below, but are not limited thereto.

[0056] The term "substitution" refers to the replacement of hydrogen atoms on carbon atoms in a compound with other substituents. There is no limitation on the position of substitution, as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0057] 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.

[0058] 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.

[0059] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, alkyl, aryl, and heterocyclic groups, or substituted by a substituent formed by linking two or more substituents of the substituents exemplified above, or having no substituents.

[0060] Examples of the above substituents are described below, but are not limited thereto.

[0061] Examples of halogen groups in this specification include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0062] In this specification, silyl groups can be represented by the chemical formula -SiYaYbYc, where Ya, Yb, and Yc can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited to these.

[0063] In this specification, the boron group can be represented by the chemical formula -BYdYe, where Yd and Ye can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the boron group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but are not limited to these.

[0064] 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.

[0065] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30. 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.

[0066] In this specification, the alkyl groups in alkylthio and alkylsulfonyl groups are subject to the above description of alkyl groups.

[0067] 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.

[0068] 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.

[0069] 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 the substituted amino group 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.

[0070] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 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.

[0071] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure.

[0072] When the aforementioned fluorene group is replaced, it can be used as follows: Isospirofluorene group; (9,9-dimethylfluorene) and Substituted fluorenyl groups such as (9,9-diphenylfluorenyl) are used. However, this is not a limitation.

[0073] In this specification, the aryl groups in aryloxy, arylthio, and arylsulfonyl groups are subject to the above description of aryl groups.

[0074] 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.

[0075] In this specification, heteroaryl refers to aromatic compounds; otherwise, the above description of heterocyclic groups applies.

[0076] In this specification, an aliphatic hydrocarbon ring refers to a non-aromatic ring composed only of carbon and hydrogen atoms. The number of carbon atoms in an aliphatic hydrocarbon ring is not particularly limited, but is preferably between 3 and 60. Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene, but are not limited to these.

[0077] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. The number of carbon atoms in an aromatic hydrocarbon ring is not particularly limited, but a number of carbon atoms from 6 to 60 is preferred. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenatene, pyrene, and tetraphenylene. The aromatic hydrocarbon rings include, but are not limited to, pentane, fluorene, indene, acenaphthene, benzo[a]fluorene, spirofluorene, etc. In this specification, the aromatic hydrocarbon ring can be interpreted in the same way as the aryl group.

[0078] In this specification, arylene refers to a group with two bonding positions in an aryl group, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the above description of aryl groups.

[0079] In this specification, a heteroaryl group refers to a heteroaryl group with two bonding sites, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the above description of heteroaryl groups.

[0080] In this specification, D represents deuterium.

[0081] In this specification, [] D＝x1～x2 The brackets indicate that the structure contains x1 to x2 deuterium atoms, each with an integer value. For example, []. D＝1～35 This indicates that it contains 1 to 35 deuterium atoms. As an example, the following structure contains 1 to 35 deuterium atoms.

[0082]

[0083] In this specification, hydrogen refers to hydrogen, deuterium, or tritium.

[0084] In one embodiment of this specification, the portion of chemical formula 1 without substituents may indicate that it is substituted with hydrogen, deuterium or tritium.

[0085] 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 will be 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, this specification, including definitions, takes precedence unless otherwise specified. Furthermore, the materials, methods, and embodiments are illustrative only and are not intended to limit the invention.

[0086] The compounds of the above chemical formula 1 will now be described in detail.

[0087] In one embodiment of this specification, L1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0088] In one embodiment of this specification, L1 is an arylene group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroarylene group with 2 to 30 substituted or unsubstituted carbon atoms.

[0089] In one embodiment of this specification, L1 is a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted divalent dibenzofuranyl.

[0090] In one embodiment of this specification, L1 is phenylene, biphenylene, naphthylene, or dibenzofuranyl.

[0091] In one embodiment of this specification, L2 to L4 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms.

[0092] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms.

[0093] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each is independently directly bonded; aryl groups are substituted or unsubstituted with one or more of deuterium, alkyl and aryl groups; or heteroaryl groups are substituted or unsubstituted with one or more of deuterium, alkyl and aryl groups.

[0094] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and are each independently directly bonded; aryl groups having 6 to 30 carbon atoms that are substituted or unsubstituted from one or more of deuterium, alkyl, and aryl groups; or heteroaryl groups having 2 to 30 carbon atoms that are substituted or unsubstituted from one or more of deuterium, alkyl, and aryl groups.

[0095] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each independently is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted divalent fluorenyl, substituted or unsubstituted divalent spirodifluorenyl, or substituted or unsubstituted divalent phenanthryl.

[0096] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each is independently directly bonded; a phenylene group substituted or unsubstituted with one or more of deuterium, alkyl, and aryl groups; a biphenylene group substituted or unsubstituted with one or more of deuterium, alkyl, and aryl groups; a terphenylene group substituted or unsubstituted with one or more of deuterium, alkyl, and aryl groups; a naphthylene group substituted or unsubstituted with one or more of deuterium, alkyl, and aryl groups; a divalent fluorene group substituted or unsubstituted with one or more of deuterium, alkyl, and aryl groups; a divalent spirodifluorene group substituted or unsubstituted with one or more of deuterium, alkyl, and aryl groups; or a divalent phenanthrene group substituted or unsubstituted with one or more of deuterium, alkyl, and aryl groups.

[0097] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each independently is a directly bonded, phenylene, biphenylene, terphenylene, naphthylene, a divalent fluorenyl group substituted or unsubstituted with one or more of alkyl and aryl groups, a divalent spirodifluorenyl group, or a divalent phenanthrene group.

[0098] In one embodiment of this specification, L4 is a directly bonded, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms.

[0099] In one embodiment of this specification, L4 is a direct bond.

[0100] In one embodiment of this specification, R1 is hydrogen or deuterium.

[0101] In one embodiment of this specification, R2 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0102] In one embodiment of this specification, R2 is an alkyl group having 1 to 30 carbon atoms that is substituted or unsubstituted, an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted, or a heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted.

[0103] In one embodiment of this specification, R2 is an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0104] In one embodiment of this specification, R2 is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, or a substituted or unsubstituted triphenylene.

[0105] In one embodiment of this specification, R2 is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted phenanthryl.

[0106] In one embodiment of this specification, R2 is a deuterated or unsubstituted phenyl group, a deuterated or unsubstituted naphthyl group, or a deuterated or unsubstituted phenanthryl group.

[0107] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted fused ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms.

[0108] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, each being independently hydrogen; deuterium; an alkyl group substituted or unsubstituted with one or more of deuterium, alkyl, and aryl; an aryl group substituted or unsubstituted with one or more of deuterium, alkyl, and aryl; a fused ring group of aromatic hydrocarbon rings and aliphatic hydrocarbon rings substituted or unsubstituted with one or more of deuterium, alkyl, and aryl; or a heteroaryl group substituted or unsubstituted with one or more of deuterium, alkyl, and aryl.

[0109] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently represents any of the following structures.

[0110]

[0111] In the above structure,

[0112] R10 to R16 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0113] The above structure is substituted with or unsubstituted by one or more substituents selected from deuterium, alkyl, and aryl.

[0114] --- is the part that combines with chemical formula 1.

[0115] In one embodiment of this specification, the structures exemplified by Ar1 and Ar2 above are substituted or unsubstituted by one or more substituents selected from deuterium, alkyl groups having 1 to 30 carbon atoms, and aryl groups having 6 to 30 carbon atoms.

[0116] In one embodiment of this specification, the structures exemplified by Ar1 and Ar2 above are substituted or unsubstituted by one or more substituents selected from deuterium, methyl, tert-butyl and phenyl.

[0117] In one embodiment of this specification, R10 to R16 may be the same as or different from each other, and each is independently an alkyl group with 1 to 30 carbon atoms that is substituted with deuterium or unsubstituted, or an aryl group with 6 to 30 carbon atoms that is substituted with deuterium or unsubstituted.

[0118] In one embodiment of this specification, R10 to R16 may be the same as or different from each other, and each is independently a methyl group that is substituted with deuterium or not substituted, or a phenyl group that is substituted with deuterium or not substituted.

[0119] In one embodiment of this specification, the compound is selected from the following structures.

[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] In one embodiment of this specification, the compound represented by the above-described chemical formula 1 can be manufactured according to the following reaction formula.

[0153] [Reaction Formula]

[0154]

[0155] In the above reaction formula, the definitions of R1 to R4, L1 to L4, r3, r4, l2, l3, Ar1 and Ar2 are the same as those in the above chemical formula 1.

[0156] In the above reaction formula, X is a halogen group. Specifically, X is Cl, Br, or I.

[0157] In this specification, compounds with various band gaps can be synthesized by introducing various substituents into the core structure as shown 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 shown above.

[0158] Furthermore, by introducing various substituents into the core structure shown above, compounds possessing the inherent properties of the introduced substituents can be synthesized. For example, by introducing substituents primarily used in hole injection materials, hole transport materials, electron blocking materials, luminescent materials, and electron transport 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] The following is a detailed explanation of organic light-emitting devices.

[0160] The organic light-emitting device according to this specification includes a first electrode, a second electrode, and one or more organic layers including a light-emitting layer disposed between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound of the 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] 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.

[0163] 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 forming an organic layer on the anode, and finally depositing a material suitable for use as the cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0164] In one embodiment of this specification, the 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. For example, when the organic light-emitting device includes a plurality of organic layers, 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.

[0165] The aforementioned organic layer can be formed from the same or different substances. Furthermore, the aforementioned organic layer can be formed using various polymer materials and through vapor deposition and / or solution processing.

[0166] In one embodiment of this specification, a multilayer organic layer is included between the first electrode and the light-emitting layer, wherein the organic layer closest to the light-emitting layer contains the aforementioned compound.

[0167] In one embodiment of this specification, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer contains the compound described above.

[0168] In one embodiment of this specification, the organic layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, hole transport layer, or electron blocking layer contains the aforementioned compound.

[0169] In one embodiment of this specification, the organic layer includes an electron blocking layer, and the electron blocking layer contains the aforementioned compound.

[0170] In one embodiment of this specification, the organic layer includes a hole transport layer, and the hole transport layer contains the aforementioned compound.

[0171] In one embodiment of this specification, the organic layer includes a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the hole transport layer or the electron blocking layer contains the aforementioned compound.

[0172] In one embodiment of this specification, the organic layer includes a light-emitting layer. In this case, the light-emitting layer may or may not contain the compound of Formula 1.

[0173] In one embodiment of this specification, the light-emitting layer comprises the compound described above.

[0174] In one embodiment of this specification, the light-emitting layer may contain the aforementioned compound as a dopant for the light-emitting layer.

[0175] In one embodiment of this specification, the light-emitting layer includes the compound described above as a dopant for the light-emitting layer, and may also include a host.

[0176] In one embodiment of this specification, the light-emitting layer includes the compound described above as a dopant for the light-emitting layer, and also includes a fluorescent host or a phosphorescent host, and may also include other organic compounds, metals or metal compounds as dopant.

[0177] In one embodiment of this specification, the light-emitting layer includes the compound as a dopant for the light-emitting layer, and also includes a fluorescent host or a phosphorescent host, and may also be used together with an iridium (Ir) dopant.

[0178] In one embodiment of this specification, the light-emitting layer may contain the compound described above as the main body of the light-emitting layer.

[0179] In one embodiment of this specification, the light-emitting layer comprises the compound as the main body of the light-emitting layer, and may also contain dopants.

[0180] In one embodiment of this specification, the organic light-emitting device includes a first electrode, a second electrode, and a light-emitting layer disposed between the first electrode and the second electrode. A single organic layer is also included between the light-emitting layer and the first electrode, and the organic layer contains a compound of the chemical formula 1.

[0181] In one embodiment of this specification, the organic light-emitting device includes a first electrode, a second electrode, and a light-emitting layer disposed between the first electrode and the second electrode. The light-emitting layer and the first electrode also include multiple organic layers, and one or more of the organic layers contain the aforementioned compound.

[0182] In one embodiment of this specification, the organic light-emitting device includes a first electrode, a second electrode, and a light-emitting layer disposed between the first electrode and the second electrode. Between the light-emitting layer and the first electrode, there is one or more of a hole injection layer, a hole transport layer, and an electron blocking layer, wherein one or more of the hole injection layer, the hole transport layer, and the electron blocking layer contains the aforementioned compound.

[0183] In one embodiment of this specification, the organic light-emitting device includes a first electrode, a second electrode, and a light-emitting layer disposed between the first electrode and the second electrode. The space between the first electrode and the light-emitting layer includes a hole injection layer, a hole transport layer, and an electron blocking layer. One or more of the hole injection layer, the hole transport layer, and the electron blocking layer contain the aforementioned compound.

[0184] For example, an organic light-emitting device according to one embodiment of this specification has a structure in which a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer and a second electrode are sequentially disposed, wherein one or more of the hole injection layer, the hole transport layer and the electron blocking layer contain the aforementioned compound.

[0185] In one embodiment of this specification, the organic light-emitting device is a structure in which a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, and a second electrode are sequentially stacked, and the hole injection layer, hole transport layer, or electron blocking layer contains the aforementioned compound.

[0186] In one embodiment of this specification, an additional organic layer may be included between the light-emitting layer and the second electrode. For example, one or more of the following may be included between the light-emitting layer and the second electrode: a hole-blocking layer, an electron injection layer, an electron transport layer, and a layer that simultaneously performs electron injection and transport.

[0187] In one embodiment of this specification, the organic light-emitting device is a structure in which a first electrode, 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 second electrode are sequentially stacked, and one or more of the hole injection layer, hole transport layer, and electron blocking layer contain the aforementioned compound.

[0188] In one embodiment of this specification, the organic light-emitting device is a structure in which a first electrode, 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 second electrode are sequentially stacked, and the hole injection layer, hole transport layer, or electron blocking layer contains the aforementioned compound.

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

[0190] In one embodiment of this specification, the first electrode is the anode and the second electrode is the cathode.

[0191] In another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0192] For example, the structure of the organic light-emitting device described in this specification can have the following characteristics: Figure 1 and 2 The structure shown is not limited to this.

[0193] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, a first electrode 2, a light-emitting layer 3, and a second electrode 4.

[0194] Figure 2 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a second electrode 4.

[0195] Specifically, in addition to the structure shown in the figure above, the organic light-emitting device may also have the following stacked structure, but is not limited to this.

[0196] (1) Anode / hole transport layer / light-emitting layer / cathode

[0197] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0198] (3) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0199] (4) Anode / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0200] (5) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode

[0201] (6) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0202] (7) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0203] (8) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0204] (9) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0205] (10) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0206] (11) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0207] (12) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0208] (13) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0209] (14) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0210] (15) 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 above-mentioned "electron transport layer / electron injection layer" can be replaced by "electron injection and transport layer" or "layer that performs electron injection and transport simultaneously".

[0212] 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 transport simultaneously".

[0213] 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.

[0214] 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 to facilitate the injection of electrons into the organic layer. Specific examples of cathode materials that can be used in this invention include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer materials such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0215] 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 accept holes from the anode at low voltages. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is 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, aryl amine compounds, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, perylene compounds, benzonitrile compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene.

[0216] Specifically, the hole injection layer described above can use arylamine compounds, quinoxaline compounds, and benzonitrile compounds. More specifically, quinoxaline compounds can be used, but are not limited to these.

[0217] In one embodiment of this specification, the hole injection layer comprises a compound with the chemical formula HI-A.

[0218] [Chemical formula HI-A]

[0219]

[0220] In the above chemical formula HI-A,

[0221] R h1 To R h6 They may be the same as or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0222] In one embodiment of this specification, the above-mentioned R h1 To R h6 Each is a cyano group.

[0223] In one embodiment of this specification, the above chemical formula HI-A has the following structure.

[0224]

[0225] 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 the hole injection characteristics from deteriorating. When it is less than 150 nm, it has the advantage of preventing the driving voltage from increasing in order to improve hole migration when the thickness of the hole injection layer is too thick.

[0226] 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 light-emitting layer; materials with high hole mobility are suitable. Specific examples of hole transport materials include, but are not limited to, compounds of Formula 1, arylamine compounds, carbazole compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions. Specifically, in the aforementioned hole transport layer, compounds of Formula 1 or carbazole compounds substituted with arylamine groups can be used, but are not limited to these. More specifically, in the aforementioned hole transport layer, compounds of Formula 1 or compounds of HT-A described below can be used.

[0227] [Chemical formula HT-A]

[0228]

[0229] In the above chemical formula HT-A,

[0230] Lx1 and Lx2 may be the same as or different from each other, and each may be a directly bonded, substituted or unsubstituted aryl group.

[0231] Rx1 to Rx5 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.

[0232] In one embodiment of this specification, Lx1 and Lx2 may be the same as or different from each other, and each may be a substituted or unsubstituted aryl group.

[0233] In one embodiment of this specification, Lx1 and Lx2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene.

[0234] In one embodiment of this specification, Lx1 and Lx2 may be the same as or different from each other, and each is independently an aryl group.

[0235] In one embodiment of this specification, Lx1 and Lx2 may be the same as or different from each other, and each is independently phenylene, biphenylene or naphthylene.

[0236] In one embodiment of this specification, Lx1 and Lx2 are each phenylene oxide.

[0237] In one embodiment of this specification, Rx1 to Rx5 may be the same as or different from each other, and each may be a substituted or unsubstituted aryl group independently.

[0238] In one embodiment of this specification, Rx1 to Rx5 may be the same as or different from each other, and each may be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.

[0239] In one embodiment of this specification, Rx1 to Rx5 may be the same as or different from each other, and each is independently an aryl group.

[0240] In one embodiment of this specification, Rx1 to Rx5 may be the same as or different from each other, and each is independently phenyl or naphthyl.

[0241] In one embodiment of this specification, the above-mentioned chemical formula HT-A has the following structure.

[0242]

[0243] An electron blocking layer may be disposed between the hole transport layer and the light-emitting layer. A phenanthrene compound or other materials known in the art can be used in the electron blocking layer. Specifically, a compound of Formula 1 or a compound in Formula 1 where L1 is directly bonded can be used in the electron blocking layer.

[0244] In one embodiment of this specification, a hole buffer layer may be further provided between the hole injection layer and the hole transport layer. The hole buffer layer may be made of materials known in the art for hole injection or transport.

[0245] In one embodiment of this specification, the light-emitting layer can emit red, green, or blue light and can be formed from a phosphorescent or fluorescent material. The light-emitting material 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 material with high quantum efficiency for fluorescence or phosphorescence. Examples of such light-emitting materials include 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds of azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spirocyclic compounds; polyfluorene; fluorene, etc., but not limited to these.

[0246] The main material of the luminescent layer can be 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, anthracene derivatives can be used as the main body of the aforementioned luminescent layer, but are not limited to these.

[0247] In one embodiment of this specification, the above-mentioned main body is represented by the following chemical formula HA.

[0248] [Chemical formula HA]

[0249]

[0250] In the above chemical formula HA,

[0251] L h1 and L h2 They may be the same as or different from each other, and each may be independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0252] R h1 and R h2 They may be the same as or different from each other, and each may be independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic groups.

[0253] R h3 It can be hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0254] r h3 The above r is an integer from 1 to 8. h3 When the value is 2 or more, there are more than 2 Rs. h3 They are the same or different from each other.

[0255] In one embodiment of this specification, the above-mentioned L h1 and L h2 They may be the same or different from each other, and each can be directly bonded or aryl independently.

[0256] In one embodiment of this specification, the above-mentioned L h1 and L h2 Each is directly bonded.

[0257] In one embodiment of this specification, the above-mentioned R h1 and R h2 They may be the same as or different from each other, and each may be an aryl group that is substituted or unsubstituted.

[0258] In one embodiment of this specification, the above-mentioned R h1 and R h2 They may be the same as or different from each other, and each may be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0259] In one embodiment of this specification, the above-mentioned R h1 and R h2 They may be the same or different from each other, and each is an aryl group independently.

[0260] In one embodiment of this specification, the above-mentioned R h1 and R h2 They may be the same as or different from each other, and each can be phenyl, biphenyl or naphthyl independently.

[0261] In one embodiment of this specification, the above-mentioned R h1 and R h2 Each is a naphthyl group.

[0262] In one embodiment of this specification, the above-mentioned R h3 It is either hydrogen or deuterium.

[0263] In one embodiment of this specification, the above-mentioned chemical formula HA has the following structure.

[0264]

[0265] When the emissive layer emits red light, phosphorescent materials such as PIQIr(acac), PQIr(acac), PQIr(tris(1-phenylisoquinoline)acetylacetone iridium, and PtOEP (platinum octaethylporphyrin) can be used as luminescent dopants, but these are not limited to them. When the emissive layer emits green light, phosphorescent materials such as Ir(ppy)3 (fac tris(2-phenylpyridine)iridium, or phosphorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used as luminescent dopants, but these are not limited to them. When the emissive 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 arylene (DSA), pyrene compounds, PFO polymers, and PPV polymers, but these are not limited to these. Specifically, pyrene compounds can be used as the aforementioned dopants, but they are not limited to these.

[0266] In one embodiment of this specification, the light-emitting layer comprises a dopant, and the dopant comprises a fluorescent dopant.

[0267] In one embodiment of this specification, the fluorescent dopant includes one or more selected from pyrene compounds and non-pyrene compounds.

[0268] In one embodiment of this specification, the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound. The pyrene-based and non-pyrene-based compounds can be used without limitation, as long as they are compounds used in this technical field.

[0269] In one embodiment of this specification, the above-mentioned pyrene compounds are represented by the following chemical formula DA.

[0270] [Chemical formula DA]

[0271]

[0272] In the above chemical formula DA,

[0273] R f1 and R f2 They may be the same as or different from each other, and each independently consists of hydrogen, deuterium, substituted or unsubstituted amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0274] rfa and rfb are each integers from 1 to 5. When rfa and rfb are 2 or more, the substituents in each bracket are the same or different from each other.

[0275] In one embodiment of this specification, the above-mentioned R f1 and R f2 They may be the same as or different from each other, and each may be an substituted or unsubstituted amino group.

[0276] In one embodiment of this specification, the above chemical formula DA is the following chemical formula DA-1.

[0277] [Chemical formula DA-1]

[0278]

[0279] In the above chemical formula DA-1,

[0280] R f3 To R f6 They may be the same or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0281] In one embodiment of this specification, the above-mentioned chemical formula DA is the following chemical formula DA-2.

[0282] [Chemical formula DA-2]

[0283]

[0284] In the above chemical formula DA-2,

[0285] R f3 R6 may be the same or different from each other, and each may be a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0286] In one embodiment of this specification, the above-mentioned R f3 R6 may be the same as or different from each other, and each may be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl.

[0287] In one embodiment of this specification, the above-mentioned R f3 R6 may be the same as or different from each other, and each may be independently a substituted or unsubstituted phenyl or a substituted or unsubstituted dibenzofuranyl.

[0288] In one embodiment of this specification, the above-mentioned chemical formula DA has the following structure.

[0289]

[0290] The aforementioned hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed using the same conditions as the hole injection layer. Specific examples of hole-blocking materials include... Diazole derivatives, triazole derivatives, triazine derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but not limited to these. Specifically, triazine derivatives can be used, but are not limited to these.

[0291] The aforementioned electron transport layer facilitates electron transport. The electron transport material is one that can effectively 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 nm 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 the driving voltage from increasing to enhance electron migration when the electron transport layer is too thick.

[0292] 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.

[0293] 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.

[0294] The electron transport layer and electron injection layer described above can be formed from a single layer. For example, electron injection material and electron transport material can be vacuum-deposited simultaneously, or materials that exhibit both electron injection and transport effects can be vacuum-deposited to form electron injection and transport layers.

[0295] In one embodiment of this specification, the electron injection and transport layer comprises a compound represented by the chemical formula ET-A, but is not limited thereto.

[0296] [Chemical formula ET-A]

[0297]

[0298] In the above chemical formula ET-A,

[0299] At least one of Z11 to Z13 is N, and the rest are CH.

[0300] At least one of Z21 to Z23 is N, and the rest are CH.

[0301] 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.

[0302] 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.

[0303] 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.

[0304] In one embodiment of this specification, L601 and L602 may be the same as or different from each other, and each is independently an aryl group.

[0305] In one embodiment of this specification, L601 and L602 are phenylene oxides.

[0306] 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.

[0307] In one embodiment of this specification, Ar601 to Ar604 may be the same as or different from each other, and each is independently an aryl group.

[0308] In one embodiment of this specification, Ar601 to Ar604 are phenyl groups.

[0309] In one embodiment of this specification, the above chemical formula ET-A is represented by the following compound.

[0310]

[0311] In one embodiment of this specification, the electron injection and transport layer may further comprise a metal complex. Examples of such metal complexes include Al complexes of 8-hydroxyquinoline (Alq3), Liq, metal coordination compounds, etc., but are not limited to these. For example, the electron injection and transport layer may use triazine derivatives and lithium quinoline (Liq), but are not limited to these.

[0312] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting device, a bottom-emitting device, or a bidirectional light-emitting device.

[0313] Furthermore, the organic light-emitting devices according to this specification can be included in various electronic devices and used. For example, the aforementioned electronic devices can be display panels, touch panels, solar modules, lighting devices, etc., and are not limited thereto.

[0314] Methods of implementing the invention

[0315] The present invention will now be described in detail with reference to specific embodiments. However, embodiments of the present invention can be modified in various different forms and should not be construed as limiting the scope of the invention to the embodiments described below. The embodiments of the present invention are provided to provide a more complete explanation of the invention to those skilled in the art.

[0316] <Synthesis example>

[0317] Synthesis Example 1. Synthesis of Compound 1

[0318]

[0319] Toluene (200 ml) was added to 10-(4-chlorophenyl)-2-phenylphenanthrene (20.00 g, 54.81 mmol), di([1,1'-biphenyl]-4-yl)amine (17.97 g, 55.91 mmol), and sodium tert-butoxide (NaOtBu) (7.37 g, 76.73 mmol), and the mixture was heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (BTP) (0.14 g, 0.27 mmol) dissolved in toluene (20 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was completed and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to give compound 1 (28.50 g, 80.02% yield). (MS [M+H]) + =650)

[0320] Synthesis Example 2. Synthesis of Compound 2

[0321]

[0322] In Synthesis Example 1 above, N-([1,1'-biphenyl]-4-yl)-[1,1':4',1”-triphenyl]-4-amine (22.23 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 2 (31.50 g, 79.17% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =726)

[0323] Synthesis Example 3. Synthesis of Compound 3

[0324]

[0325] In Synthesis Example 1 above, N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (17.97 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 3 (28.00 g, 78.61% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =650)

[0326] Synthesis Example 4. Synthesis of Compound 4

[0327]

[0328] In Synthesis Example 1 above, N-phenyl-[1,1':4',1”-triphenyl]-4-amine (17.97 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 4 (28.00 g, 78.61% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =650)

[0329] Synthesis Example 5. Synthesis of Compound 5

[0330]

[0331] In Synthesis Example 1 above, N-([1,1'-biphenyl]-2-yl)-[1,1':4',1”-triphenyl]-4-amine (22.23 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 5 (32.00 g, 80.42% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =726)

[0332] Synthesis Example 6. Synthesis of Compound 6

[0333]

[0334] In Synthesis Example 1 above, N-([1,1'-biphenyl]-3-yl)-[1,1':4',1”-triphenyl]-4-amine (22.23 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 6 (31.00 g, 77.91% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =726)

[0335] Synthesis Example 7. Synthesis of Compound 7

[0336]

[0337] In Synthesis Example 1 above, N-(4-(naphthyl-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (20.77 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 7 (31.00 g, 80.81% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =700)

[0338] Synthesis Example 8. Synthesis of Compound 8

[0339]

[0340] In Synthesis Example 1 above, N-(4-(naphthyl-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (20.77 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 8 (30.50 g, 79.51% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =700)

[0341] Synthesis Example 9. Synthesis of Compound 9

[0342]

[0343] In Synthesis Example 1 above, bis(4-(naphthyl-1-yl)phenyl)amine (23.57 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 9 (32.50 g, 79.07% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =750)

[0344] Synthesis Example 10. Synthesis of Compound 10

[0345]

[0346] In Synthesis Example 1 above, 4-(phenanthrene-9-yl)-N-phenylaniline (19.31 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 10 (29.50 g, 79.87% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =674)

[0347] Synthesis Example 11. Synthesis of Compound 11

[0348]

[0349] In Synthesis Example 1 above, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorenyl-2-amine (20.21 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 11 (29.00 g, 76.69% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =690)

[0350] Synthesis Example 12. Synthesis of Compound 12

[0351]

[0352] In Synthesis Example 1 above, 2'-(9H-carbazol-9-yl)-N-phenyl-[1,1'-biphenyl]-4-amine (22.95 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 12 (31.50 g, 77.78% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =739)

[0353] Synthesis Example 13. Synthesis of Compound 13

[0354]

[0355] In Synthesis Example 1 above, N-(2'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (27.21 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine, and compound 13 (35.00 g, 78.35% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =815)

[0356] Synthesis Example 14. Synthesis of Compound 14

[0357]

[0358] In Synthesis Example 1 above, N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furanyl-3-amine (18.75 g, 55.91 mmol) was used instead of di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 14 (28.50 g, 78.33% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =664)

[0359] Synthesis Example 15. Synthesis of Compound 15

[0360]

[0361] In Synthesis Example 1 above, 10-(4-chlorophenyl)-2-(naphth-1-yl)phenanthrene (20.00 g, 48.20 mmol) and di([1,1'-biphenyl]-4-yl)amine (15.80 g, 49.16 mmol) were used instead of 10-(4-chlorophenyl)-2-phenylphenanthrene and di([1,1'-biphenyl]-4-yl)amine, and compound 15 (26.50 g, 78.55% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =700)

[0362] Synthesis Example 16. Synthesis of Compound 16

[0363]

[0364] In Synthesis Example 1 above, 10-(4-chlorophenyl)-2-(naphth-1-yl)phenanthrene (20.00 g, 48.20 mmol) and N-([1,1'-biphenyl]-2-yl)-[1,1':4',1”-triphenyl]-4-amine (19.54 g, 49.16 mmol) were used instead of 10-(4-chlorophenyl)-2-phenylphenanthrene and di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 16 (30.00 g, 80.21% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =776)

[0365] Synthesis Example 17. Synthesis of Compound 17

[0366]

[0367] In Synthesis Example 1 above, 10-(4-chlorophenyl)-2-(naphth-2-yl)phenanthrene (20.00 g, 48.20 mmol) and di([1,1'-biphenyl]-4-yl)amine (15.80 g, 49.16 mmol) were used instead of 10-(4-chlorophenyl)-2-phenylphenanthrene and di([1,1'-biphenyl]-4-yl)amine, and compound 17 (26.50 g, 78.55% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =700)

[0368] Synthesis Example 18. Synthesis of Compound 18

[0369]

[0370] In Synthesis Example 1 above, 10-(4-chlorophenyl)-2-(naphth-2-yl)phenanthrene (20.00 g, 48.20 mmol) and N-([1,1'-biphenyl]-2-yl)-[1,1':4',1”-triphenyl]-4-amine (19.54 g, 49.16 mmol) were used instead of 10-(4-chlorophenyl)-2-phenylphenanthrene and di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 18 (30.00 g, 80.21% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =776)

[0371] Synthesis Example 19. Synthesis of Compound 19

[0372]

[0373] In Synthesis Example 1 above, 10-(3-chlorophenyl)-2-phenylphenanthrene (20.00 g, 54.81 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1”-triphenyl]-4-amine (22.23 g, 55.91 mmol) were used instead of 10-(4-chlorophenyl)-2-phenylphenanthrene and di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 19 (31.50 g, 79.17% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =726)

[0374] Synthesis Example 20. Synthesis of Compound 20

[0375]

[0376] In Synthesis Example 1 above, 10-(3-chlorophenyl)-2-phenylphenanthrene (20.00 g, 54.81 mmol) and N-([1,1'-biphenyl]-2-yl)-[1,1':4',1”-triphenyl]-4-amine (22.23 g, 55.91 mmol) were used instead of 10-(4-chlorophenyl)-2-phenylphenanthrene and di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 20 (32.00 g, 80.42% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =726)

[0377] Synthesis Example 21. Synthesis of Compound 21

[0378]

[0379] In Synthesis Example 1 above, 10-(3-chlorophenyl)-2-phenylphenanthrene (20.00 g, 54.81 mmol) and N-(4-(naphthyl-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (20.77 g, 55.91 mmol) were used instead of 10-(4-chlorophenyl)-2-phenylphenanthrene and di([1,1'-biphenyl]-4-yl)amine, and compound 21 (31.00 g, 80.81% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =700)

[0380] Synthesis Example 22. Synthesis of Compound 22

[0381]

[0382] In Synthesis Example 1 above, 10-(3-chlorophenyl)-2-phenylphenanthrene (20.00 g, 54.81 mmol) and N-(4-(naphthyl-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (20.77 g, 55.91 mmol) were used instead of 10-(4-chlorophenyl)-2-phenylphenanthrene and di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 22 (30.00 g, 78.20% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =700)

[0383] Synthesis Example 23. Synthesis of Compound 23

[0384]

[0385] In Synthesis Example 1 above, 10-(3-chlorophenyl)-2-phenylphenanthrene (20.00 g, 54.81 mmol) and 2'-(9H-carbazol-9-yl)-N-phenyl-[1,1'-biphenyl]-4-amine (22.95 g, 55.91 mmol) were used instead of 10-(4-chlorophenyl)-2-phenylphenanthrene and di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 23 (32.00 g, 79.01% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =739)

[0386] Synthesis Example 24. Synthesis of Compound 24

[0387]

[0388] In Synthesis Example 1 above, 10-(2-chlorophenyl)-2-phenylphenanthrene (20.00 g, 54.81 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1”-triphenyl]-4-amine (22.23 g, 55.91 mmol) were used instead of 10-(4-chlorophenyl)-2-phenylphenanthrene and di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 24 (30.50 g, 76.65% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =726)

[0389] Synthesis Example 25. Synthesis of Compound 25

[0390]

[0391] In Synthesis Example 1 above, 10-(2-chlorophenyl)-2-phenylphenanthrene (20.00 g, 54.81 mmol) and N-([1,1'-biphenyl]-2-yl)-[1,1':4',1”-triphenyl]-4-amine (22.23 g, 55.91 mmol) were used instead of 10-(4-chlorophenyl)-2-phenylphenanthrene and di([1,1'-biphenyl]-4-yl)amine. Otherwise, compound 25 (30.50 g, 76.65% yield) was obtained by the same method as in Synthesis Example 1 above. (MS[M+H) + =726)

[0392] Synthesis Example 26. Synthesis of Compound 26

[0393]

[0394] Compound 2 (20.0 g, 27.55 mmol) obtained in Synthetic Example 2 was added to benzene-d6 (200 ml) and completely dissolved. Trifluoromethanesulfonic acid (CF3SO3H) (1.2 ml, 13.8 mmol) was then added, and the mixture was stirred for 25 minutes. After the reaction was complete, dichloromethane was added, and the mixture was subjected to layer separation to obtain the organic layer. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and recrystallized from ethyl acetate to obtain compound 26 (16.0 g, 77.84%). (MS [M+H]) + =746)

[0395] Synthesis Example 27. Synthesis of Compound 27

[0396]

[0397] In Synthesis Example 26 above, compound 5 (20.0 g, 27.55 mmol) obtained in Synthesis Example 5 above was used instead of compound 2. Otherwise, compound 27 (16.00 g, 77.84% yield) was obtained by the same method as in Synthesis Example 26 above. (MS[M+H)) + =746)

[0398] Synthesis Example 28. Synthesis of Compound 28

[0399]

[0400] In Synthesis Example 26 above, compound 7 (20.0 g, 28.58 mmol) obtained in Synthesis Example 7 above was used instead of compound 2. Otherwise, compound 28 (16.50 g, 80.29% yield) was obtained by the same method as in Synthesis Example 26 above. (MS[M+H)) + =719)

[0401] Synthesis Example 29. Synthesis of Compound 29

[0402]

[0403] In Synthesis Example 26 above, compound 2 was replaced with compound 8 (20.0 g, 28.58 mmol) obtained in Synthesis Example 8 above. Otherwise, compound 29 (16.50 g, 80.29% yield) was obtained by the same method as in Synthesis Example 26 above. (MS[M+H)) + =719)

[0404] Synthesis Example 30. Synthesis of Compound 30

[0405]

[0406] In Synthesis Example 26 above, compound 10 (20.0 g, 29.68 mmol) obtained in Synthesis Example 10 above was used instead of compound 2. Otherwise, compound 30 (16.00 g, 78.17% yield) was obtained by the same method as in Synthesis Example 26 above. (MS[M+H) + =692)

[0407] Synthesis Example 31. Synthesis of Compound 31

[0408]

[0409] In Synthesis Example 26 above, compound 12 (20.0 g, 27.07 mmol) obtained in Synthesis Example 12 above was used instead of compound 2. Otherwise, compound 31 (16.50 g, 80.41% yield) was obtained by the same method as in Synthesis Example 26 above. (MS[M+H)) + =758)

[0410] Synthesis Example 32. Synthesis of Compound 32

[0411]

[0412] In Synthesis Example 26 above, compound 19 (20.0 g, 27.55 mmol) obtained in Synthesis Example 19 above was used instead of compound 2. Otherwise, compound 32 (16.00 g, 77.84% yield) was obtained by the same method as in Synthesis Example 26 above. (MS[M+H)) + =746)

[0413] Synthesis Example 33. Synthesis of Compound 33

[0414]

[0415] In Synthesis Example 26 above, compound 20 (20.0 g, 27.55 mmol) obtained in Synthesis Example 20 above was used instead of compound 2. Otherwise, compound 33 (16.00 g, 77.84% yield) was obtained by the same method as in Synthesis Example 26 above. (MS[M+H)) + =746)

[0416] <Experimental Examples and Comparative Examples>

[0417] Experimental Example 1-1

[0418] ITO (Indium Tin Oxide) 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.

[0419] On the ITO transparent electrode prepared in this way, a compound represented by the chemical formula HAT will be applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. On the aforementioned hole injection layer, a compound represented by the chemical formula HT1 is used as a hole transport layer. After vacuum evaporation to a thickness of [amount], compound 1 manufactured in the above synthesis example 1 is used as an electron blocking layer. The thickness is achieved by thermal vacuum evaporation. Next, as the luminescent layer, a compound represented by the chemical formula BH and a compound represented by the chemical formula BD are mixed in a weight ratio of 25:1. Vacuum evaporation is performed to a thickness of [amount missing]. Next, as a hole-blocking layer, a compound represented by the chemical formula HB1 is [deposited / applied]. Vacuum evaporation was performed on the thickness. Next, as an electron injection and transport layer, a compound represented by the chemical formula ET1 and a compound represented by Liq were applied in a 1:1 weight ratio. The thickness is achieved through thermal vacuum evaporation. On the aforementioned electron injection and transport layer, lithium fluoride (LiF) is sequentially deposited... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness, thereby manufacturing organic light-emitting devices.

[0420]

[0421] Experimental Examples 1-2 to 1-33 and Comparative Examples 1-1 to 1-7.

[0422] In Experiment 1-1 above, the compound listed in Table 1 below was used instead of compound 1, and the organic light-emitting device was otherwise fabricated using the same method as in Experiment 1-1 above.

[0423] The compounds EB1 to EB7 used in the comparative examples are shown below.

[0424]

[0425] An application of 10 mA / cm² was applied to the organic light-emitting devices fabricated in the experimental and comparative examples. 2 At the given current, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nits) to 95%.

[0426] [Table 1]

[0427]

[0428]

[0429] As shown in Table 1 above, the compounds of the present invention have been confirmed to have excellent electron blocking capabilities, and organic light-emitting devices using them as electron blocking layers exhibit the effects of reduced driving voltage, high efficiency, and excellent lifetime.

[0430] Conversely, when it can be confirmed that L1 in chemical formula 1 is directly bonded (Comparative Examples 1-1, 1-2), phenanthrene 2 or 10 is not substituted (Comparative Examples 1-3 to 1-5), or substituents are present at other positions of phenanthrene (Comparative Examples 1-6, 1-7), the driving voltage increases, efficiency decreases, and lifetime decreases compared to the examples.

[0431] Experimental Examples 2-1 to 2-33 and Comparative Examples 1-1, 2-1 to 2-6.

[0432] In Experiment 1-1 above, as the electron blocking layer, the compound represented by the above chemical formula EB1 was used instead of compound 1, and as the hole transport layer, the compound listed in Table 2 below was used instead of the compound represented by the above chemical formula HT1. Otherwise, an organic light-emitting device was fabricated by the same method as in Experiment 1-1 above.

[0433] The compounds HT2 to HT7 used in the comparative examples are shown below.

[0434]

[0435] An application of 10 mA / cm² was applied to the organic light-emitting devices fabricated in the experimental and comparative examples. 2 At the given current, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nits) to 95%.

[0436] [Table 2]

[0437]

[0438]

[0439] As shown in Table 2 above, the compounds of the present invention have been confirmed to have excellent hole transport capabilities, and organic light-emitting devices using them as hole transport layers exhibit the effects of reduced driving voltage, high efficiency, and excellent lifetime.

[0440] Conversely, it can be confirmed that when phenanthrene is not present (Comparative Example 2-1), L1 in Formula 1 is directly bonded (Comparative Example 2-2), the second or tenth position of phenanthrene is not substituted (Comparative Examples 2-3 to 2-5), or substituents are present at other positions of phenanthrene (Comparative Examples 2-6, 2-7), the driving voltage increases and the efficiency and lifetime decrease compared to the examples.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, L1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. L2 to L4 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R1, R3, and R4 may be the same as or different from each other, and each can be hydrogen or deuterium independently. R2 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Ar1 and Ar2 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aromatic hydrocarbon rings with fused rings of aliphatic hydrocarbon rings, or substituted or unsubstituted heteroaryl. r3 is an integer from 1 to 4. When r3 is 2 or higher, two or more R3 values ​​are the same or different from each other. r4 is an integer from 1 to 3. When r4 is 2 or higher, two or more R4 values ​​are the same or different from each other. l2 and l3 are each integers from 1 to 3. When l2 is 2 or more, two or more L2s are the same or different from each other. When l3 is 2 or more, two or more L3s are the same or different from each other.

2. The compound according to claim 1, wherein, R2 is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, or a substituted or unsubstituted triphenylene.

3. The compound according to claim 1, wherein, The L1 is a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted divalent dibenzofuranyl.

4. The compound according to claim 1, wherein, The L2 and L3 may be the same as or different from each other, and are each independently directly bonded; aryl groups having 6 to 30 carbon atoms that are substituted or unsubstituted by one or more of deuterium, alkyl, and aryl groups; or heteroaryl groups having 2 to 30 carbon atoms that are substituted or unsubstituted by one or more of deuterium, alkyl, and aryl groups.

5. The compound according to claim 1, wherein, The L2 and L3 may be the same as or different from each other, and each independently is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted divalent fluorenyl, substituted or unsubstituted divalent spirodifluorenyl, or substituted or unsubstituted divalent phenanthryl.

6. The compound according to claim 1, wherein, The Ar1 and Ar2 may be the same as or different from each other, and each is independently hydrogen; deuterium; an alkyl group substituted or unsubstituted with one or more of deuterium, alkyl and aryl; an aryl group substituted or unsubstituted with one or more of deuterium, alkyl and aryl; a fused ring group of aromatic hydrocarbon rings and aliphatic hydrocarbon rings substituted or unsubstituted with one or more of deuterium, alkyl and aryl; or a heteroaryl group substituted or unsubstituted with one or more of deuterium, alkyl and aryl.

7. The compound according to claim 1, wherein, Ar1 and Ar2 may be the same as or different from each other, and each independently constitutes any of the following structures: In the structure, R10 to R16 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. The structure is substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, and aryl. --- is the part that combines with chemical formula 1.

8. The compound according to claim 1, wherein, The compound is selected from the following structures:

9. An organic light-emitting device, comprising: First electrode, Second electrode, and The organic layer consists of one or more layers, including a light-emitting layer disposed between the first electrode and the second electrode. 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 hole injection layer, a hole transport layer, or an electron blocking layer, wherein the hole injection layer, the hole transport layer, or the electron blocking layer contains the compound.

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

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