Compound and organic light-emitting element comprising same

Abstract

The present specification relates to a compound represented by chemical formula 1, and an organic light-emitting element comprising same. Specifically, the compound comprises pyrene substituted with a naphthofuran group or a naphthothiophene group, the organic light-emitting element comprises: a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprise the compound.

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of Korean Patent Application No. 10-2023-0185761 filed with the Korean Intellectual Property Office on December 19, 2023, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to a compound and an organic light-emitting device comprising the same.

[0003] In general, organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light emitting devices that utilize the organic light emitting phenomenon typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

[0004] There is a continuing need for the development of new materials for organic light-emitting devices such as the above.

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

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

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

[0010] One to four of R2 to R5 and R7 to R10 are bonded to the following chemical formula 2,

[0011] The remaining R2 to R5 and R7 to R10 are the same or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0012] R1 and R6 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0013] [Chemical Formula 2]

[0014]

[0015] In the above chemical formula 2,

[0016] X is O or S,

[0017] A1, A2 and R11 are the same or different and are each independently hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0018] L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0019] l1 is an integer from 1 to 4, and if l1 is 2 or greater, two or more L1 are equal to or different from each other,

[0020] r11 is an integer from 1 to 5, and when r11 is 2, 2 or more R11 are equal to or different from each other,

[0021] * is a part that is bonded to the above chemical formula 1.

[0022] Another embodiment of the present specification provides an organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the compound described above.

[0023] A compound according to one embodiment of the present specification can be used in an organic light-emitting device, thereby reducing the operating voltage of the organic light-emitting device and improving its efficiency. In addition, the thermal stability of the compound can improve the lifespan characteristics of the device.

[0024] Figures 1 to 5 illustrate examples of organic light-emitting devices according to some embodiments of the present specification.

[0025] Figure 6 is a diagram showing the MS graph of compound A.

[0026] [Explanation of symbols]

[0027] 1: Substrate

[0028] 2: First electrode

[0029] 3: Second electrode

[0030] 4: Emissive layer

[0031] 4-1: First light-emitting layer

[0032] 4-2: Second light-emitting layer

[0033] 5: Hole injection layer

[0034] 6: Hole transport layer

[0035] 6-1: First hole transport layer

[0036] 6-2: Second hole transport layer

[0037] 7: Electronic control layer

[0038] 8: Electron transport layer

[0039] 9: Electron injection layer

[0040] 10: Organic layer

[0041] One embodiment of the present specification provides a compound of the above chemical formula 1.

[0042] The compound of chemical formula 1 according to one embodiment of the present specification is a pyrene-based compound substituted with chemical formula 2, and by including chemical formula 2, it can lead to improvement in the injection, transport, and control characteristics of holes and electrons.

[0043] Below, to aid understanding, the terms used in this specification are explained in more detail.

[0044] In this specification, when a part is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0045] In this specification, when it is said that a member is located “on” another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0046] In this specification, the term "layer" is interchangeable with the term "film," which is commonly used in the present technical field, and refers to a coating covering a desired area. The size of the "layer" is not limited, and each "layer" may be the same or different in size. In one embodiment, the size of the "layer" may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

[0047] In this specification, "or" means an inclusive "or" and not an exclusive "or." For example, a condition A or B is satisfied by either: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0048] In this specification, the meaning of a specific A material being included in a B layer includes both i) one or more A materials being included in one B layer and ii) the B layer being composed of one or more layers, and the A material being included in one or more layers of the multiple B layers.

[0049] In this specification, the meaning that a specific A material is included in a C layer or a D layer means that the A material is i) included in at least one layer among at least one C layer, ii) included in at least one layer among at least one D layer, or iii) included in at least one C layer and at least one D layer, respectively.

[0050] In the present invention, “*” and " " means a portion that is connected to each other as a substituent or bonding group.

[0051] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0052] The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group (-CN); a nitro group; a hydroxyl group; an alkyl group; a cycloalkyl group; an alkoxy group; a phosphine oxide group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; an alkenyl group; a silyl group; a boron group; an amine group; an aryl group; and a heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are connected, or having no substituents. For example, "a substituent connected with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are connected.

[0053] The term "substituted or unsubstituted" in this specification means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; silyl group; alkoxy group; aryloxy group; alkyl group; aryl group; and heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

[0054] The term "substituted or unsubstituted" in this specification means substituted with one or more substituents selected from the group consisting of deuterium; alkyl groups; aryl groups; and heterocyclic groups, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

[0055] In this specification, the connection of two or more substituents means that the hydrogen of one substituent is connected to another substituent. For example, the connection of two substituents means that a phenyl group and a naphthyl group are connected. or can be a substituent of. In addition, the connection of three substituents includes not only the case where (substituent 1)-(substituent 2)-(substituent 3) are connected sequentially, but also the case where (substituent 2) and (substituent 3) are connected to (substituent 1). For example, a phenyl group, a naphthyl group, and an isopropyl group are connected. , , or can be a substituent. The above definition also applies to cases where four or more substituents are connected.

[0056] Examples of the above substituents are described below, but are not limited thereto.

[0057] In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0058] In the present specification, a 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. The carbon number of the silyl group is not particularly limited, but is preferably 1 to 30 carbon atoms, or 3 to 30 carbon atoms. Examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.

[0059] In the present specification, the boron group may be represented by the chemical formula -BYdYe, wherein Yd and Ye may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Examples of the boron group include, but are not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, and a phenyl boron group.

[0060] In the present specification, the alkyl group may be straight-chain or branched. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 60 carbon atoms. Examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an n-pentyl group, a hexyl group, an n-hexyl group, a heptyl group, an n-heptyl group, an octyl group, and an n-octyl group.

[0061] In the present specification, the alkoxy group may be straight-chain, branched-chain or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Examples of the alkoxy group include, but are not limited to, 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.

[0062] Substituents comprising alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight-chain and branched forms.

[0063] In the present specification, the alkenyl group may be linear or branched. The carbon number of the alkenyl group is not particularly limited, but is preferably 2 to 40 carbon atoms. Examples of the alkenyl group include, but are not limited to, 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, and styrenyl.

[0064] In the present specification, the carbon number of the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms. Examples of the cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantane group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.1]octyl group, a norbornyl group, and the like.

[0065] In the present specification, the amine group is -NH2, and the amine group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The carbon number of the amine group is not particularly limited, but is preferably 1 to 30 carbon atoms. Examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, a diphenylamine group, a phenylpyridylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, a dibenzofuranylphenylamine group, a 9-methylanthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like.

[0066] In the present specification, the number of carbon atoms in the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms. In addition, the aryl group may be a monocyclic aryl group or a polycyclic aryl group. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaternary phenyl group, etc. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, anthracenyl group, a phenanthrene group, a benzophenanthrene group, a pyrene group, a chrysene group, a fluorenyl group, a triphenylene group, etc.

[0067] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

[0068] When the above fluorenyl group is substituted, , Spirofluorenyl group of etc. (9,9-dimethylfluorenyl group), and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group), but is not limited thereto.

[0069] In this specification, the aryl group among the aryloxy groups may be applied to the description of the aryl group described above.

[0070] In the present specification, a heterocyclic group is a ring group containing at least one of N, O, P, S, Si, and Se as a heteroatom. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like.

[0071] In this specification, the description of the heterocyclic group described above may be applied, except that the heteroaryl group is aromatic.

[0072] In the present specification, in a ring formed by adjacent groups bonding to each other, “ring” means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0073] In the present specification, the hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring.

[0074] In this specification, an aliphatic hydrocarbon ring means a ring that is not aromatic and is composed only of carbon and hydrogen atoms. The number of carbon atoms in the aliphatic hydrocarbon ring is not particularly limited, but is preferably 3 to 60 carbon atoms. Examples of the aliphatic hydrocarbon ring include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc.

[0075] In this specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms. The number of carbon atoms in the aromatic hydrocarbon ring is not particularly limited, but is preferably 6 to 60 carbon atoms. Examples of the aromatic hydrocarbon ring include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, etc.

[0076] In this specification, an aromatic hydrocarbon ring group can be interpreted as having the same meaning as an aryl group.

[0077] In this specification, an arylene group means a group having two bonding positions to an aryl group, i.e., a divalent group. The description of the aryl group described above may be applied to these groups, except that each is a divalent group.

[0078] In this specification, a heteroarylene group means a group having two bonding positions to a heteroaryl group, i.e., a divalent group. The description of the heteroaryl group described above may be applied to each of these groups, except that they are each divalent groups.

[0079] In this specification, D means deuterium.

[0080] In this specification, [ ] D=x1~x2means that the structure within the parentheses contains x1 to x2 deuterium atoms, and the value is an integer. For example, [ ] D=0~16 means that it contains 0 to 16 deuterium atoms. As an example, the structure below contains 0 to 16 deuterium atoms.

[0081]

[0082] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, this specification, including definitions, will control unless a specific passage is cited. Furthermore, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0083] Hereinafter, the compound of the above chemical formula 1 will be described in detail.

[0084] In one embodiment of the present specification, one of R2 to R5 and R7 to R10 is bonded to the chemical formula 2.

[0085] In one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-1 or 1-2.

[0086]

[0087] In the above chemical formulas 1-1 and 1-2,

[0088] R1 to R10 are the same or different and are each independently hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0089] is a part that is combined with the above chemical formula 2.

[0090] In one embodiment of the present specification, two of R2 to R5 and R7 to R10 are combined with the chemical formula 2.

[0091] In one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 1-11 to 1-20.

[0092]

[0093]

[0094] In the above chemical formulas 1-11 to 1-20,

[0095] R1 to R10 are the same or different and are each independently hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0096] is a part that is combined with the above chemical formula 2.

[0097] In one embodiment of the present specification, three of R2 to R5 and R7 to R10 are combined with the chemical formula 2.

[0098] In one embodiment of the present specification, four of R2 to R5 and R7 to R10 are combined with the chemical formula 2.

[0099] In one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 1-31 to 1-35.

[0100]

[0101] In the above chemical formulas 1-31 to 1-35,

[0102] R1 and R3 to R10 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0103] is a part that is combined with the above chemical formula 2.

[0104] In one embodiment of the present specification, 1 to 4 of R2 to R5 and R7 to R10 are combined with the chemical formula 2, and the remaining R2 to R5 and R7 to R10 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0105] That is, the remainder of R2 to R5 and R7 to R10 that are not combined with chemical formula 2 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0106] For example, R2 is combined with chemical formula 2, and the remaining R3 to R5 and R7 to R10 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0107] In one embodiment of the present specification, 1 to 4 of R2 to R5 and R7 to R10 are combined with the chemical formula 2, and the remaining R2 to R5 and R7 to R10 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted silyl group having 3 to 30 carbon atoms; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0108] In one embodiment of the present specification, 1 to 4 of R2 to R5 and R7 to R10 are combined with the chemical formula 2, and the remaining R2 to R5 and R7 to R10 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0109] In one embodiment of the present specification, 1 to 4 of R2 to R5 and R7 to R10 are combined with the chemical formula 2, and the remaining R2 to R5 and R7 to R10 are the same as or different from each other, and are each independently hydrogen; deuterium; an aryl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; or a heterocyclic group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group.

[0110] In one embodiment of the present specification, 1 to 4 of R2 to R5 and R7 to R10 are combined with the chemical formula 2, and the remaining R2 to R5 and R7 to R10 are the same as or different from each other, and are each independently hydrogen; deuterium; 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 phenanthrene group; a substituted or unsubstituted benzophenanthrene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0111] In one embodiment of the present specification, 1 to 4 of R2 to R5 and R7 to R10 are combined with the chemical formula 2, and the remaining R2 to R5 and R7 to R10 are the same as or different from each other, and each independently hydrogen; deuterium; a phenyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; a biphenyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; a terphenyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; a naphthyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; a phenanthrene group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; A benzophenanthrene group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; a dibenzofuran group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; or a dibenzothiophene group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group.

[0112] In one embodiment of the present specification, 1 to 4 of R2 to R5 and R7 to R10 are combined with the chemical formula 2, and the remaining R2 to R5 and R7 to R10 are the same as or different from each other, and each independently hydrogen; deuterium; a phenyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an aryl group, and a heterocyclic group; a biphenyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an aryl group, and a heterocyclic group; a terphenyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an aryl group, and a heterocyclic group; a naphthyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an aryl group, and a heterocyclic group; a phenanthrene group unsubstituted or substituted with at least one selected from the group consisting of deuterium, an aryl group, and a heterocyclic group; A benzophenanthrene group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an aryl group, and a heterocyclic group; a dibenzofuran group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an aryl group, and a heterocyclic group; or a dibenzothiophene group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an aryl group, and a heterocyclic group.

[0113] In one embodiment of the present specification, 1 to 4 of R2 to R5 and R7 to R10 are combined with the chemical formula 2, and the remaining R2 to R5 and R7 to R10 are the same as or different from each other, and each independently hydrogen; deuterium; a phenyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, a naphthyl group, a dibenzofuran group, and a dibenzothiophene group; a biphenyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, a naphthyl group, a dibenzofuran group, and a dibenzothiophene group; a terphenyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, a naphthyl group, a dibenzofuran group, and a dibenzothiophene group; a naphthyl group unsubstituted or substituted with at least one selected from the group consisting of deuterium, a phenyl group, a naphthyl group, a dibenzofuran group, and a dibenzothiophene group; A phenanthrene group unsubstituted or substituted with at least one selected from the group consisting of a deuterium atom, a phenyl group, a naphthyl group, a dibenzofuran group, and a dibenzothiophene group; a benzophenanthrene group unsubstituted or substituted with at least one selected from the group consisting of a deuterium atom, a phenyl group, a naphthyl group, a dibenzofuran group, and a dibenzothiophene group; a dibenzofuran group unsubstituted or substituted with at least one selected from the group consisting of a deuterium atom, a phenyl group, and a naphthyl group; or a dibenzothiophene group unsubstituted or substituted with at least one selected from the group consisting of a deuterium atom, a phenyl group, and a naphthyl group.

[0114] In one embodiment of the present specification, R1 and R6 are the same as or different from each other, and each independently represent hydrogen; deuterium; 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 phenanthrene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0115] In one embodiment of the present specification, R1 and R6 are the same as or different from each other, and are each independently hydrogen; deuterium; 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 phenanthrene group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

[0116] In one embodiment of the present specification, R1 and R6 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0117] In one embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0118] In one embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0119] In one embodiment of the present specification, A1 and A2 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0120] In one embodiment of the present specification, the chemical formula 2 is any one of the following chemical formulas 2-1 to 2-3.

[0121] [Chemical Formula 2-1]

[0122]

[0123] [Chemical Formula 2-2]

[0124]

[0125] [Chemical Formula 2-3]

[0126]

[0127] In the above chemical formulas 2-1 to 2-3,

[0128] X is O or S,

[0129] L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0130] A1, A2, R12 and R13 are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0131] l1 is an integer from 1 to 4, and if l1 is 2 or greater, two or more L1 are equal to or different from each other,

[0132] r12 is 1 or 2, r13 is an integer from 1 to 4, r12+r13 is an integer from 1 to 5, and when r12 and r13 are 2 or greater, the substituents in each parenthesis are the same or different,

[0133] * is a part that is bonded to the above chemical formula 1.

[0134] In one embodiment of the present specification, the chemical formula 2-1 is any one of the following chemical formulas 2-1-1 to 2-1-6.

[0135] [Chemical Formula 2-1-1]

[0136]

[0137] [Chemical Formula 2-1-2]

[0138]

[0139] [Chemical Formula 2-1-3]

[0140]

[0141] [Chemical Formula 2-1-4]

[0142]

[0143] [Chemical Formula 2-1-5]

[0144]

[0145] [Chemical Formula 2-1-6]

[0146]

[0147] In the above chemical formulas 2-1-1 to 2-1-6,

[0148] X, L1, A1, A2 and l1 are the same as defined in the above chemical formula 2,

[0149] R12 and R13 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0150] r12 is 1 or 2, and when r12 is 2, the substituents in the parentheses are the same or different,

[0151] r13' is an integer from 1 to 3, r13 is an integer from 1 to 4, and when r13 and r13' are 2 or more, the substituents in each parenthesis are the same or different,

[0152] * is a part that is bonded to the above chemical formula 1.

[0153] In one embodiment of the present specification, the chemical formula 2-2 is any one of the following chemical formulas 2-2-1 to 2-2-6.

[0154] [Chemical Formula 2-2-1]

[0155]

[0156] [Chemical Formula 2-2-2]

[0157]

[0158] [Chemical Formula 2-2-3]

[0159]

[0160] [Chemical Formula 2-2-4]

[0161]

[0162] [Chemical Formula 2-2-5]

[0163]

[0164] [Chemical Formula 2-2-6]

[0165]

[0166] In the above chemical formulas 2-2-1 to 2-2-6,

[0167] X, L1, A1, A2 and l1 are the same as defined in the above chemical formula 2,

[0168] R12 and R13 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0169] r12 is 1 or 2, and when r12 is 2, the substituents in the parentheses are the same or different,

[0170] r13' is an integer from 1 to 3, r13 is an integer from 1 to 4, and when r13 and r13' are 2 or more, the substituents in each parenthesis are the same or different,

[0171] * is a part that is bonded to the above chemical formula 1.

[0172] In one embodiment of the present specification, the chemical formula 2-3 is any one of the following chemical formulas 2-3-1 to 2-3-6.

[0173] [Chemical Formula 2-3-1]

[0174]

[0175] [Chemical Formula 2-3-2]

[0176]

[0177] [Chemical Formula 2-3-3]

[0178]

[0179] [Chemical Formula 2-3-4]

[0180]

[0181] [Chemical Formula 2-3-5]

[0182]

[0183] [Chemical Formula 2-3-6]

[0184]

[0185] In the above chemical formulas 2-3-1 to 2-3-6,

[0186] X, L1, A1, A2 and l1 are the same as defined in the above chemical formula 2,

[0187] R12 and R13 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0188] r12 is 1 or 2, and when r12 is 2, the substituents in the parentheses are the same or different,

[0189] r13' is an integer from 1 to 3, r13 is an integer from 1 to 4, and when r13 and r13' are 2 or more, the substituents in each parenthesis are the same or different,

[0190] * is a part that is bonded to the above chemical formula 1.

[0191] In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0192] In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted divalent dibenzofuran group; or a substituted or unsubstituted divalent dibenzothiophene group.

[0193] In one embodiment of the present specification, L1 is a direct bond; a phenylene group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; a biphenylene group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; a naphthylene group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; a divalent dibenzofuran group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; or a divalent dibenzothiophene group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group.

[0194] In one embodiment of the present specification, L1 is a direct bond; a phenylene group unsubstituted or substituted with one or more selected from the group consisting of deuterium and aryl groups; a biphenylene group unsubstituted or substituted with one or more selected from the group consisting of deuterium and aryl groups; a naphthylene group unsubstituted or substituted with one or more selected from the group consisting of deuterium and aryl groups; a divalent dibenzofuran group unsubstituted or substituted with one or more selected from the group consisting of deuterium and aryl groups; or a divalent dibenzothiophene group unsubstituted or substituted with one or more selected from the group consisting of deuterium and aryl groups.

[0195] In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted divalent dibenzofuran group.

[0196] In one embodiment of the present specification, L1 is a direct bond; a phenylene group unsubstituted or substituted with one or more selected from the group consisting of deuterium and aryl groups; a biphenylene group unsubstituted or substituted with one or more selected from the group consisting of deuterium and aryl groups; a naphthylene group unsubstituted or substituted with one or more selected from the group consisting of deuterium and aryl groups; or a divalent dibenzofuran group unsubstituted or substituted with one or more selected from the group consisting of deuterium and aryl groups.

[0197] In one embodiment of the present specification, L1 is a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; or a divalent dibenzofuran group substituted or unsubstituted with deuterium.

[0198] In one embodiment of the present specification, R11 is hydrogen; deuterium; a substituted or unsubstituted silyl group having 3 to 30 carbon atoms; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0199] In one embodiment of the present specification, R11 is hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0200] In one embodiment of the present specification, R11 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0201] In one embodiment of the present specification, R11 is hydrogen; or deuterium.

[0202] In one embodiment of the present specification, R12 and R13 are the same as or different from each other, and each independently represent hydrogen; deuterium; a substituted or unsubstituted silyl group having 3 to 30 carbon atoms; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0203] In one embodiment of the present specification, R12 and R13 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0204] In one embodiment of the present specification, R12 and R13 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0205] In one embodiment of the present specification, R12 and R13 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0206] In one embodiment of the present specification, the compound of chemical formula 1 contains at least one deuterium.

[0207] In one embodiment of the present specification, the compound of the chemical formula 1 has a deuterium substitution rate of 10% or more.

[0208] In one embodiment of the present specification, the compound of the chemical formula 1 has a deuterium substitution rate of 20% or more.

[0209] In one embodiment of the present specification, the compound of chemical formula 1 has a deuterium substitution rate of 30% or more.

[0210] In one embodiment of the present specification, the compound of chemical formula 1 has a deuterium substitution rate of 40% or more.

[0211] In one embodiment of the present specification, the upper limit of the deuterium substitution rate of the compound of the chemical formula 1 is not limited, but may be, for example, 100% or less, or less than 100%.

[0212] For example, the deuterium substitution rate of the above chemical formula 1 is 10% to 100%.

[0213] As used herein, “containing deuterium,” “deuterated,” or “deuterated” means that a hydrogen at a substitutable position of a compound is replaced with deuterium.

[0214] As used herein, “perdeuterated” means a compound or group in which all hydrogens in the molecule are replaced with deuterium, and has the same meaning as “100% deuterated.”

[0215] In the present specification, “X% deuterated”, “degree of deuteration X%”, or “deuterium substitution rate X%” means that X% of the hydrogens at substitutable positions in the structure are replaced with deuterium. For example, when the structure is dibenzofuran, “25% deuterated” of the dibenzofuran, “degree of deuteration 25%” of the dibenzofuran, or “deuterium substitution rate 25%” of the dibenzofuran means that 2 of the 8 hydrogens at substitutable positions of the dibenzofuran are replaced with deuterium.

[0216] In this specification, "degree of deuteration" or "deuterium substitution rate" refers to the degree of deuteration as measured by nuclear magnetic resonance spectroscopy ( 1 It can be confirmed by known methods such as H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0217] Specifically, nuclear magnetic resonance spectroscopy ( 1 When analyzing the "degree of deuteration" or "deuterium substitution rate" by H NMR, add DMF (dimethylformamide) as an internal standard.1 Through the integration ratio on H NMR, the degree of deuteration or deuterium substitution can be calculated from the total peak integration amount.

[0218] In addition, when analyzing the "degree of deuteration" or "deuterium substitution rate" through TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the distribution of molecular weights at the end of the reaction. For example, when analyzing the degree of deuteration of the following compound A, when the molecular weight of the following starting material is 506 and the maximum value (median value) of the molecular weight of the following compound A is 527 in the MS graph of FIG. 6, since 21 of the hydrogens (26) at the substitutable positions of the following starting material were substituted with deuterium, it can be calculated that approximately 81% of the hydrogens were deuterated.

[0219]

[0220] In one embodiment of the present specification, the compound of chemical formula 1 has one of the following structures.

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229] One embodiment of the present specification provides an organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound of the chemical formula 1.

[0230] The organic layer of the organic light-emitting device of the present specification may be formed as a single-layer structure, but may also be formed as a multi-layer structure in which two or more organic layers are laminated. For example, it may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, an electron control layer, a hole control layer, etc. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0231] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

[0232] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host of the light-emitting layer.

[0233] In one embodiment of the present specification, the light-emitting layer includes two or more types of hosts.

[0234] In one embodiment of the present specification, the light-emitting layer includes two or more mixed hosts, and at least one of the two or more mixed hosts includes a compound of the chemical formula 1.

[0235] In one embodiment of the present specification, the light-emitting layer includes two or more mixed hosts, one of the two or more mixed hosts includes the compound of the above chemical formula 1, and the remaining include anthracene compounds. In this case, the anthracene compound may be used without limitation as long as it is an anthracene host used in the art.

[0236] In this specification, an anthracene compound means a compound containing anthracene.

[0237] In one embodiment of the present specification, the light-emitting layer includes two types of hosts.

[0238] In one embodiment of the present specification, the light-emitting layer includes two types of hosts, and at least one type of the hosts includes a compound of the chemical formula 1.

[0239] In one embodiment of the present specification, the light-emitting layer includes the compound as a first host and further includes a second host of the following chemical formula H.

[0240] [Chemical formula H]

[0241]

[0242] In the above chemical formula H,

[0243] R100 to R109 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

[0244] In one embodiment of the present specification, R100 to R109 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0245] In one embodiment of the present specification, R100 to R109 are the same as or different from each other, and are each independently hydrogen; deuterium; an unsubstituted aryl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an aryl group, and a heteroaryl group; or a heteroaryl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, an aryl group, and a heteroaryl group.

[0246] In one embodiment of the present specification, R100 to R107 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0247] In one embodiment of the present specification, R108 and R109 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0248] In one embodiment of the present specification, R108 and R109 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0249] In one embodiment of the present specification, R108 and R109 are the same as or different from each other, and are each independently an unsubstituted aryl group substituted or unsubstituted with one or more selected from the group consisting of deuterium, an aryl group, and a heteroaryl group; or a heteroaryl group substituted or unsubstituted with one or more selected from the group consisting of deuterium, an aryl group, and a heteroaryl group.

[0250] In one embodiment of the present specification, the chemical formula H has one of the following structures.

[0251]

[0252]

[0253]

[0254] In one embodiment of the present specification, when the host of the light-emitting layer includes the first host and the second host, the mass ratio of the first host and the second host may be 99:1 to 1:99, 90:10 to 10:90, 80:20 to 20:80, 70:30 to 30:70, or 60:40 to 40:60.

[0255] An organic light-emitting device using two or more mixed hosts according to one embodiment of the present specification is intended to improve the performance of the device by mixing the advantages of each host. For example, when mixing two hosts, an organic light-emitting device having the effects of high efficiency, low voltage, and long life can be manufactured by mixing one host having the effects of high efficiency and low voltage and one host having the effects of long life.

[0256] In one embodiment of the present specification, the light-emitting layer has two or more layers, and at least one layer among the two or more light-emitting layers includes the compound of the chemical formula 1.

[0257] In one embodiment of the present specification, the light-emitting layer has two or more layers, and at least one layer of the two or more light-emitting layers includes two or more types of mixed hosts, and at least one type of the two or more types of mixed hosts includes the compound of the chemical formula 1.

[0258] In one embodiment of the present specification, the organic light-emitting device includes two light-emitting layers (bilayers).

[0259] In one embodiment of the present specification, the light-emitting layer is a bilayer, and at least one of the two light-emitting layers includes the compound of the chemical formula 1.

[0260] In one embodiment of the present specification, the light-emitting layer is a bilayer, and one of the two light-emitting layers includes the compound of the chemical formula 1.

[0261] In one embodiment of the present specification, the two light-emitting layers are provided in contact with each other.

[0262] In one embodiment of the present specification, the light-emitting layer includes a first light-emitting layer provided between the first electrode and the second electrode; and a second light-emitting layer provided between the first light-emitting layer and the second electrode and in contact with the first light-emitting layer, wherein either the first light-emitting layer or the second light-emitting layer includes a compound of the chemical formula 1.

[0263] In one embodiment of the present specification, the light-emitting layer includes a first light-emitting layer provided between the first electrode and the second electrode; and a second light-emitting layer provided between the first light-emitting layer and the second electrode and in contact with the first light-emitting layer, wherein one of the first light-emitting layer and the second light-emitting layer includes a compound of the chemical formula 1, and the other includes a compound of the chemical formula H.

[0264] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0265] In one embodiment of the present specification, the light-emitting layer includes a first light-emitting layer provided between the anode and the cathode; and a second light-emitting layer provided between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein either the first light-emitting layer or the second light-emitting layer includes a compound of the chemical formula 1.

[0266] In one embodiment of the present specification, the first light-emitting layer includes a compound of the chemical formula 1, and the second light-emitting layer includes a compound of the chemical formula H.

[0267] That is, the light-emitting layer includes a first light-emitting layer provided between the anode and the cathode; and a second light-emitting layer provided between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein the first light-emitting layer includes a compound of the chemical formula 1, and the second light-emitting layer includes a compound of the chemical formula H.

[0268] In one embodiment of the present specification, the first light-emitting layer includes a compound of the chemical formula H, and the second light-emitting layer includes a compound of the chemical formula 1.

[0269] That is, the light-emitting layer includes a first light-emitting layer provided between the anode and the cathode; and a second light-emitting layer provided between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein the first light-emitting layer includes a compound of the chemical formula H, and the second light-emitting layer includes a compound of the chemical formula 1.

[0270] In one embodiment of the present specification, the first light-emitting layer includes the compound of the chemical formula 1 as a host of the first light-emitting layer.

[0271] In one embodiment of the present specification, the first light-emitting layer includes a compound of the chemical formula H as a host of the first light-emitting layer.

[0272] In one embodiment of the present specification, the second light-emitting layer includes the compound of the chemical formula 1 as a host of the second light-emitting layer.

[0273] In one embodiment of the present specification, the second light-emitting layer includes a compound of the chemical formula H as a host for the second light-emitting layer.

[0274] In one embodiment of the present specification, at least one of the first light-emitting layer and the second light-emitting layer each includes two or more types of mixed hosts. In this case, the specific description of the two or more types of mixed hosts is the same as described above.

[0275] In one embodiment of the present specification, the first light-emitting layer includes two or more hosts, and one of the two or more hosts is a compound of the chemical formula 1.

[0276] In one embodiment of the present specification, the second light-emitting layer includes two or more hosts, and one of the two or more hosts is a compound of the chemical formula 1.

[0277] In one embodiment of the present specification, the second light-emitting layer includes two or more hosts, and one of the two or more hosts is a compound of the chemical formula H.

[0278] In one embodiment of the present specification, the first light-emitting layer includes two types of hosts, and one of the two types of hosts is a compound of the chemical formula 1.

[0279] In one embodiment of the present specification, the second light-emitting layer includes two types of hosts, and one of the two types of hosts is a compound of the chemical formula 1.

[0280] In one embodiment of the present specification, the second light-emitting layer includes two types of hosts, and one of the two types of hosts is a compound of the chemical formula H.

[0281] In one embodiment of the present specification, the maximum emission peak (λ) of the light-emitting layer including the compound of the chemical formula 1 max ) is 400 nm to 470 nm.

[0282] In one embodiment of the present specification, the thickness of the light-emitting layer is not limited, but is, for example, 3 nm to 100 nm. Specifically, it is 3 nm to 80 nm, 3 nm to 60 nm, or 3 nm to 30 nm.

[0283] In one embodiment of the present specification, the thickness of the first light-emitting layer and the second light-emitting layer can be applied without limitation as long as it is a thickness that can suppress the first light-emitting layer (singlet light-emitting region) and the second light-emitting layer (TTF light-emitting region) from overlapping. For example, the thickness of the first light-emitting layer and the second light-emitting layer is 3 nm to 50 nm, respectively. Specifically, it is 3 nm to 30 nm, 3 nm to 15 nm, or 3 nm to 10 nm. When the thickness of the light-emitting layer satisfies the above range, it is easy to separate the singlet light-emitting region and the light-emitting region derived from the TTF, and it is easy to suppress the phenomenon of the host material of the light-emitting layer being lost.

[0284] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant.

[0285] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the host includes a compound represented by the chemical formula 1.

[0286] In one embodiment of the present specification, the dopant is a blue dopant.

[0287] In one embodiment of the present specification, the dopant material includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, the dopant material includes, but is not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

[0288] In one embodiment of the present specification, the dopant includes a fluorescent dopant.

[0289] In one embodiment of the present specification, the fluorescent dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound.

[0290] In one embodiment of the present specification, the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound.

[0291] The above pyrene-based compounds and non-pyrene-based compounds can be used without limitation as long as they are compounds used in the art.

[0292] In one embodiment of the present specification, the fluorescent dopant is a non-pyrene compound.

[0293] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes a compound represented by the chemical formula 1, and the dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound.

[0294] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes a compound represented by the chemical formula 1, and the dopant includes a non-pyrene-based compound.

[0295] In one embodiment of the present specification, the non-pyrene compound includes at least one of a boron compound and a diamine compound.

[0296] In one embodiment of the present specification, the boron compound is represented by the following chemical formula D or E.

[0297] In one embodiment of the present specification, the diamine compound is represented by the following chemical formula F.

[0298] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes a compound represented by the chemical formula 1, and the dopant includes at least one compound among the following chemical formulas D, E, and F.

[0299] [Chemical Formula D]

[0300]

[0301] [Chemical Formula E]

[0302]

[0303] [Chemical formula F]

[0304]

[0305] In the above chemical formulas D, E and F,

[0306] Y1 to Y4 are the same or different from each other, and are each independently CR' or NR", and at least one of Y1 and Y2 and at least one of Y3 and Y4 is NR",

[0307] Z1 to Z4 are the same or different and each independently represent a substituted or unsubstituted 5-membered ring; a substituted or unsubstituted 6-membered ring; or a condensed ring of a substituted or unsubstituted 5-membered ring and a 6-membered ring,

[0308] R401, R402, R' and R" are the same or different and each independently represent hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0309] Lx is a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group, provided that Lx is not a divalent pyrene group;

[0310] Ar101 to Ar104 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0311] r401 and r402 are each an integer from 1 to 3, and when r401 and r402 are 2 or more, the substituents in each parenthesis are the same or different.

[0312] In one embodiment of the present specification, the chemical formula D is one of the following structures.

[0313]

[0314]

[0315]

[0316] In one embodiment of the present specification, the chemical formula F is represented by the following chemical formula F-1.

[0317] [Chemical Formula F-1]

[0318]

[0319] In the above chemical formula F-1,

[0320] Ar101 to Ar104 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0321] Rd1 and Rd2 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0322] rd1 and rd2 are each integers from 1 to 6, and when rd1 and rd2 are 2 or greater, the substituents in each parenthesis are the same or different.

[0323] In one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0324] In one embodiment of the present specification, Ar101 to Ar104 are the same as 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 terphenyl group; or a substituted or unsubstituted naphthyl group.

[0325] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes the compound, and the dopant includes a compound of the chemical formula D or chemical formula E.

[0326] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes the compound, and the dopant includes a compound of the chemical formula D or chemical formula F.

[0327] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes the compound, and the dopant includes the compound of the chemical formula D.

[0328] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes the compound, and the dopant includes the compound of the chemical formula F.

[0329] In one embodiment of the present specification, the light-emitting layer includes host:dopant in a weight ratio of 50:50 to 99.9:0.1.

[0330] In one embodiment of the present specification, the organic light-emitting device is a blue organic light-emitting device.

[0331] In one embodiment of the present specification, the organic light-emitting device further includes one or two 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, an electron injection layer, an electron control layer, a hole blocking layer, and an electron blocking layer.

[0332] In one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode; a light-emitting layer provided between the first electrode and the second electrode; and an additional organic layer provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0333] In one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode; a light-emitting layer provided between the first electrode and the second electrode; and two or more organic layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0334] In one embodiment of the present specification, two or more organic layers between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, may be selected from the group consisting of an additional light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron blocking layer, a hole blocking layer, an electron control layer, a hole control layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

[0335] In one embodiment of the present specification, the two or more organic layers may be the same organic layer. For example, the two or more organic layers may be a first hole transport layer and a second hole transport layer, and the first hole transport layer and the second hole transport layer may contain the same or different materials.

[0336] In one embodiment of the present specification, the first electrode is an anode or a cathode.

[0337] In one embodiment of the present specification, the second electrode is a cathode or an anode.

[0338] In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0339] In one embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0340] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is illustrated in FIGS. 1 to 4. FIGS. 1 to 4 illustrate the organic light-emitting device and are not limited thereto.

[0341] Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode (2), an organic layer (10), and a second electrode (3) are sequentially laminated.

[0342] Figure 2 illustrates the structure of an organic light-emitting device in which a first electrode (2), a light-emitting layer (4), and a second electrode (3) are sequentially laminated on a substrate (1).

[0343] FIG. 3 illustrates the structure of an organic light-emitting device in which a first electrode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (4), an electron control layer (7), an electron transport layer (8), an electron injection layer (9), and a second electrode (3) are sequentially laminated on a substrate (1).

[0344] FIG. 4 illustrates the structure of an organic light-emitting device in which a first electrode (2), a hole injection layer (5), a hole transport layer (6), a first light-emitting layer (4-1), a second light-emitting layer (4-2), an electron control layer (7), an electron transport layer (8), an electron injection layer (9), and a second electrode (3) are sequentially laminated on a substrate (1).

[0345] FIG. 5 illustrates the structure of an organic light-emitting device in which a first electrode (2), a hole injection layer (5), a first hole transport layer (6-1), a second hole transport layer (6-2), a first light-emitting layer (4-1), a second light-emitting layer (4-2), an electron control layer (7), an electron transport layer (8), an electron injection layer (9), and a second electrode (3) are sequentially laminated on a substrate (1).

[0346] In one embodiment of the present specification, the compound is included in the light-emitting layer.

[0347] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that the light-emitting layer, the first light-emitting layer, and / or the second light-emitting layer include the compound of the above-described chemical formula 1.

[0348] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0349] The organic light-emitting device of the present specification can be manufactured using a conventional organic light-emitting device manufacturing method and material, except that the light-emitting layer is formed using the compound represented by the above-described chemical formula 1.

[0350] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. In addition to this method, the organic light-emitting device can be manufactured by sequentially depositing a second electrode material, an organic layer, and a first electrode material on the substrate.

[0351] In addition, the compound represented by the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

[0352] In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing an organic layer, a first electrode material, and a second electrode material on a substrate. However, the manufacturing method is not limited to this.

[0353] As the first electrode material, a material having a high work function is generally preferred so that hole injection into the organic layer can be facilitated. Examples thereof include, but are not limited to, 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.

[0354] The second electrode material is preferably a material having a low work function to facilitate electron injection into the organic layer. Examples thereof include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structures such as LiF / Al or LiO2 / Al;

[0355] The above-described light-emitting layer may include a host material and a dopant material. In the case where an additional light-emitting layer is included in addition to the light-emitting layer including the compound of Chemical Formula 1 according to one embodiment of the present specification, the host material may be a condensed and / or non-condensed aromatic ring derivative or a heterocycle-containing compound. Specifically, examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocycle-containing compounds include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like. The dopant material is as described above.

[0356] The above hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes, thereby having a hole receiving effect from the anode and an excellent hole injection effect into the light-emitting layer or light-emitting material. In addition, a material having an excellent ability to prevent excitons generated in the light-emitting layer from moving to the electron injection layer or electron injection material is preferable. In addition, a material having an excellent thin film forming ability is preferable. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrines, oligothiophenes, arylamine compounds, quinoxaline compounds, hexanitrilehexaazatriphenylene compounds, quinacridone compounds, perylene compounds, benzonitrile compounds, anthraquinones, and conductive polymers of polyaniline and polythiophene series.

[0357] In one embodiment of the present specification, the hole injection layer includes a compound of the following chemical formula HI-A.

[0358] [Chemical formula HI-A]

[0359]

[0360] In the above chemical formula HI-A,

[0361] R h1 Inland R h6 are the same or different from each other, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0362] In one embodiment of the present specification, the R h1 Inland R h6 are each cyano groups.

[0363] In one embodiment of the present specification, the chemical formula HI-A has the following structure.

[0364]

[0365] The above-mentioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is preferably a material with high hole mobility that can receive holes from the anode or the hole injection layer and transport them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic compounds, carbazole-based organic compounds, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0366] In one embodiment of the present specification, the hole transport layer includes at least one compound of the following chemical formulas HT-1 and HT-2.

[0367] [Chemical formula HT-1]

[0368]

[0369] [Chemical formula HT-2]

[0370]

[0371] In the above chemical formulas HT-1 and HT-2,

[0372] Rs1 to Rs5 are the same or different and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0373] Ls1 and Ls2 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,

[0374] Ars1 to Ars4 are the same or different and each independently represent a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0375] rs2, rs4 and rs5 are each an integer from 1 to 4, rs3 is an integer from 1 to 3, and when rs2 to rs5 are each 2 or greater, the substituents in each parenthesis are the same or different.

[0376] In one embodiment of the present specification, Rs1 to Rs5 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0377] In one embodiment of the present specification, Ls1 and Ls2 are the same as or different from each other, and each independently represents a substituted or unsubstituted arylene group.

[0378] In one embodiment of the present specification, Ls1 and Ls2 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0379] In one embodiment of the present specification, Ars1 to Ars4 are the same as 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 terphenyl group; or a substituted or unsubstituted naphthyl group.

[0380] In one embodiment of the present specification, the HT-1 has the following structure.

[0381]

[0382] In one embodiment of the present specification, the HT-2 has the following structure.

[0383]

[0384] 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.

[0385] According to one embodiment of the present specification, the first hole transport layer may include a compound of the chemical formula HT-1.

[0386] According to one embodiment of the present specification, the second hole transport layer may include a compound of the chemical formula HT-2.

[0387] The above hole control layer is a layer that can improve the lifespan and efficiency of the device by controlling the smooth injection of holes transported from the hole transport layer into the light-emitting layer and preventing electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer. Known materials can be used without limitation, and can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.

[0388] The above electron control layer is a layer that controls the smooth injection of electrons transferred from the electron transport layer into the light-emitting layer, and any known material can be used without limitation.

[0389] In one embodiment of the present specification, the electron control layer includes a substituted or unsubstituted xanthene group; or a substituted or unsubstituted spirofluorolene-9,9'-xanthene group.

[0390] In one embodiment of the present specification, the electronic control layer includes a compound of the following chemical formula EB-A.

[0391] [Chemical formula EB-A]

[0392]

[0393] In the above chemical formula EB-A,

[0394] Rb1 and Rb2 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0395] rb1 and rb2 are each integers from 1 to 8, and when rb1 and rb2 are each integers greater than or equal to 2, the substituents in each parenthesis are the same or different.

[0396] In one embodiment of the present specification, Rb1 and Rb are the same as or different from each other, and each independently represent hydrogen; deuterium; or an aryl group substituted or unsubstituted with a substituted or unsubstituted heteroaryl group.

[0397] In one embodiment of the present specification, Rb1 is hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0398] In one embodiment of the present specification, Rb1 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

[0399] In one embodiment of the present specification, Rb1 is a phenyl group substituted with hydrogen; deuterium; or a substituted heteroaryl group.

[0400] In one embodiment of the present specification, Rb1 is a phenyl group substituted with hydrogen; deuterium; or a heteroaryl group substituted with an aryl group.

[0401] In one embodiment of the present specification, Rb1 is a phenyl group substituted with hydrogen; deuterium; or a triazine group substituted with an aryl group.

[0402] In one embodiment of the present specification, Rb2 is hydrogen; or deuterium.

[0403] In one embodiment of the present specification, the chemical formula EB-A has the following structure.

[0404]

[0405] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is preferable. For example, the electron transport material includes, but is not limited to, organic compounds selected from fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, and anthrone, and their derivatives; metal complex compounds; and nitrogen-containing 5-membered ring derivatives.

[0406] The above metal complex compounds include lithium quinolate (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-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

[0407] In one embodiment of the present specification, the electron transport layer may use an organic compound and a metal complex at the same time.

[0408] In one embodiment of the present specification, the electron transport layer includes a compound represented by the following chemical formula ET-A.

[0409] [Chemical formula ET-A]

[0410]

[0411] In the above chemical formula ET-A,

[0412] At least one of Z11 to Z13 is N, and the rest are CH,

[0413] At least one of Z21 to Z23 is N, and the rest are CH,

[0414] L601 and L602 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0415] Ar601 to Ar604 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0416] In one embodiment of the present specification, L601 and L602 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0417] In one embodiment of the present specification, L601 and L602 are the same as or different from each other, and each independently is an arylene group.

[0418] In one embodiment of the present specification, L601 and L602 are phenylene groups.

[0419] In one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0420] In one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and each independently is an aryl group.

[0421] In one embodiment of the present specification, Ar601 to Ar604 are substituted or unsubstituted phenyl groups.

[0422] In one embodiment of the present specification, Ar601 to Ar604 are phenyl groups substituted or unsubstituted with cyano group.

[0423] In one embodiment of the present specification, the chemical formula ET-A is any one of the following compounds.

[0424]

[0425] The above electron injection layer is a layer that receives electrons from the electrode. The electron injection material preferably has excellent electron transport ability, an electron receiving effect from the second electrode, and an excellent electron injection effect for the light-emitting layer or light-emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferred. Specific examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0426] The above metal complex compounds include 8-hydroxyquinolinato lithium, 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, Examples include, but are not limited to, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc.

[0427] The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. Known materials can be used without limitation, and can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.

[0428] The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0429] The above capping layer is formed to prevent a significant amount of light from being lost through total reflection in the organic light-emitting element, and the capping layer has the performance to sufficiently protect the lower cathode and light-emitting layer from external moisture penetration or contamination, has a high refractive index, can prevent light loss due to total reflection, and can use conventional materials without limitation.

[0430] The organic light-emitting device according to the present specification may be a front-emitting, back-emitting or double-sided emitting device depending on the material used.

[0431] The organic light-emitting device according to the present specification can be incorporated into and used in various electronic devices. For example, the electronic devices may be, but are not limited to, display panels, touch panels, solar modules, lighting devices, etc.

[0432] Hereinafter, the present specification will be described in detail with examples and comparative examples. However, the examples and comparative examples according to the present specification may be modified in various different forms, and the scope of the present specification is not construed as being limited to the examples and comparative examples described below. The examples and comparative examples of the present specification are provided to more fully explain the present specification to those with average knowledge in the art.

[0433] <Manufacturing Example>

[0434] Manufacturing Example 1. Synthesis of Intermediate A

[0435]

[0436] Manufacturing Example 1-1) Synthesis of intermediate A-1

[0437] After adding SM1 (1 eq) and SM2 (1.1 eq) to tetrahydrofuran (THF, 10 times that of SM1), 2 M potassium carbonate aqueous solution (30% volume ratio compared to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added, and the mixture was heated and stirred for 10 hours. After lowering the temperature to room temperature and completing the reaction, the potassium carbonate aqueous solution was separated and removed, and THF was distilled under reduced pressure. After dissolving it in chloroform, it was placed in a separatory funnel, washed three times with distilled water, and the organic layer was dried over anhydrous magnesium sulfate. After that, chloroform was removed under reduced pressure, and recrystallized from hexane to obtain intermediate A-1 in a solid state.

[0438] Manufacturing Example 1-2) Synthesis of intermediate A

[0439] Intermediate A-1 (1 eq.) and bis(pinacolato)diboron (1.5 eq.) were added to 1,4-dioxane (12 times that of Intermediate A-1), potassium acetate (3.0 eq.) was added, and the mixture was stirred and refluxed. Palladium acetate (0.02 eq.) and tricyclohexylphosphine (0.04 eq.) were added to 1,4-dioxane after stirring for 5 minutes, and after confirming the completion of the reaction after 2 hours, the mixture was cooled to room temperature. After removing 1,4-dioxane by distillation under reduced pressure, ethanol and water were added, filtered, and purified by recrystallization with ethyl acetate and ethanol to prepare Intermediate A.

[0440] Manufacturing Example 2. Synthesis of Intermediate B

[0441]

[0442] Manufacturing Example 2-1) Synthesis of Intermediate B-1

[0443] Intermediate B-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0444] Manufacturing Example 2-2) Synthesis of Intermediate B

[0445] Intermediate B was manufactured by synthesizing in the same manner as in Manufacturing Example 1-2, except that Intermediate B-1 was used instead of Intermediate A-1 in Manufacturing Example 1-2.

[0446] Manufacturing Example 3. Synthesis of Intermediate C

[0447]

[0448] Manufacturing Example 3-1) Synthesis of intermediate C-1

[0449] Intermediate C-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0450] Manufacturing Example 3-2) Synthesis of intermediate C

[0451] Intermediate C was prepared by synthesizing in the same manner as in Manufacturing Example 1-2, except that Intermediate C-1 was used instead of Intermediate A-1 in Manufacturing Example 1-2.

[0452] Manufacturing Example 4. Synthesis of Intermediate D

[0453]

[0454] Manufacturing Example 4-1) Synthesis of intermediate D-1

[0455] literature<ACS Appl. Mater. Interfaces 2017, 9, 15, 13785> Intermediate D-1 was obtained by synthesis as described above.

[0456] Manufacturing Example 4-2) Synthesis of intermediate D

[0457] Intermediate D was prepared by synthesizing in the same manner as in Manufacturing Example 1-2, except that Intermediate D-1 was used instead of Intermediate A-1 in Manufacturing Example 1-2.

[0458] Manufacturing Example 5. Synthesis of Intermediate E

[0459]

[0460] Manufacturing Example 5-1) Synthesis of intermediate E-1

[0461] Intermediate E-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0462] Manufacturing Example 5-2) Synthesis of intermediate E

[0463] Intermediate E was manufactured in the same manner as in Manufacturing Example 1-2, except that Intermediate E-1 was used instead of Intermediate A-1 in Manufacturing Example 1-2.

[0464] Manufacturing Example 6. Synthesis of Intermediate F

[0465]

[0466] Manufacturing Example 6-1) Synthesis of intermediate F-1

[0467] Intermediate F-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0468] Manufacturing Example 6-2) Synthesis of intermediate F

[0469] Intermediate F was manufactured by synthesizing in the same manner as in Manufacturing Example 1-2, except that Intermediate F-1 was used instead of Intermediate A-1 in Manufacturing Example 1-2.

[0470] Manufacturing Example 7. Synthesis of Compound BH-1

[0471]

[0472] Manufacturing Example 7-1) Synthesis of compound BH-1-1

[0473] Compound BH-1-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0474] Manufacturing Example 7-2) Synthesis of compound BH-1

[0475] Compound BH-1-1 and AlCl3 (20% wt) were added to C6D6 (20 times the amount of compound BH-1-1) and stirred for 2 hours. After the reaction was completed, D2O (1.5 times the amount of compound BH-1-1) was added and stirred for 30 minutes, and then trimethylamine (1 / 10 times the amount of D2O) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4 and recrystallized from ethyl acetate to prepare compound BH-1.

[0476] Manufacturing Example 8. Synthesis of compound BH-2

[0477]

[0478] Manufacturing Example 8-2) Synthesis of compound BH-2

[0479] Compound BH-2 was prepared by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0480] Manufacturing Example 9. Synthesis of compound BH-3

[0481]

[0482] Compound BH-3 was prepared by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0483] Manufacturing Example 10. Synthesis of compound BH-4

[0484]

[0485] Manufacturing Example 10-1) Synthesis of compound BH-4-1

[0486] Compound BH-4-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that 1-bromo-3-chlorobenzene and intermediate F were used instead of SM1 and SM2 in Manufacturing Example 1-1.

[0487] Manufacturing Example 10-2) Synthesis of compound BH-4-2

[0488] Compound BH-4-2 was obtained by synthesizing in the same manner as in Manufacturing Example 1-2, except that compound BH-4-1 was used instead of intermediate A-1 in Manufacturing Example 1-2.

[0489] Manufacturing Example 10-3) Synthesis of compound BH-4-3

[0490] Compound BH-4-3 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that 1-bromopyrene and compound BH-4-2 were used instead of SM1 and SM2 in Manufacturing Example 1-1.

[0491] Manufacturing Example 10-4) Synthesis of compound BH-4

[0492] Compound BH-4 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-4-3 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0493] Manufacturing Example 11. Synthesis of compound BH-5

[0494]

[0495] Manufacturing Example 11-1) Synthesis of compound BH-5-1

[0496] Compound BH-5-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0497] Manufacturing Example 11-2) Synthesis of compound BH-5

[0498] Compound BH-5 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-5-1 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0499] Manufacturing Example 12. Synthesis of compound BH-6

[0500]

[0501] Manufacturing Example 12-1) Synthesis of compound BH-6-1

[0502] Compound BH-6-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0503] Manufacturing Example 12-2) Synthesis of compound BH-6-2

[0504] Compound BH-6-1 (1 eq.) was dissolved in acetonitrile (AN, 20 times that of compound BH-6-1), and then potassium carbonate (2.5 eq.) aqueous solution (30% wt) was added. Then, 1.5 eq. of nonafluorobutan-1-sulfonic fluoride was slowly added dropwise while stirring (room temperature). After confirming the completion of the reaction after 5 hours, the acetonitrile was removed by distillation under reduced pressure, and the mixture was dissolved in chloroform and extracted several times with water. The organic layer was dried over anhydrous magnesium sulfate, distilled under reduced pressure to remove the organic solvent, and purified by recrystallization using ethanol to prepare compound BH-6-2.

[0505] Manufacturing Example 12-3) Synthesis of compound BH-6-3

[0506] Compound BH-6-3 was obtained by synthesizing in the same manner as in Manufacturing Example 1-2, except that compound BH-6-2 was used instead of intermediate A-1 in Manufacturing Example 1-2.

[0507] Manufacturing Example 12-4) Synthesis of compound BH-6-4

[0508] Compound BH-6-4 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that 7-chloronaphthofuran and compound BH-6-3 were used instead of SM1 and SM2 in Manufacturing Example 1-1.

[0509] Manufacturing Example 12-5) Synthesis of compound BH-6

[0510] Compound BH-6 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-6-4 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0511] Manufacturing Example 13. Synthesis of Compound BH-7

[0512]

[0513] Manufacturing Example 13-1) Synthesis of compound BH-7-1

[0514] SM1 (1,8-dibromopyrene, 1 eq) and SM2 (intermediate E, 2.2 eq) were added to tetrahydrofuran (THF, 10 times the amount of 1,8-dibromopyrene), followed by addition of 2 M potassium carbonate aqueous solution (30% volume ratio compared to THF), followed by addition of tetrakistriphenyl-phosphinopalladium (2 mol%), and heated and stirred for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was separated and removed, and THF was distilled under reduced pressure. After dissolving in chloroform, the mixture was placed in a separatory funnel, washed three times with distilled water, and the organic layer was dried over anhydrous magnesium sulfate. Afterwards, chloroform was removed under reduced pressure, and recrystallized from EA (Ethyl Acetate) to obtain compound BH-7-1 in a solid state.

[0515] Manufacturing Example 13-2) Synthesis of compound BH-7

[0516] Compound BH-7 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-7-1 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0517] Manufacturing Example 14. Synthesis of compound BH-8

[0518]

[0519] Manufacturing Example 14-1) Synthesis of compound BH-8-1

[0520] Compound BH-8-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0521] Manufacturing Example 14-2) Synthesis of compound BH-8-2

[0522] Compound BH-8-2 was obtained by synthesizing in the same manner as in Manufacturing Example 12-2, except that compound BH-8-1 was used instead of compound BH-6-1 in Manufacturing Example 12-2.

[0523] Manufacturing Example 14-3) Synthesis of compound BH-8-3

[0524] Compound BH-8-3 was obtained by synthesizing in the same manner as in Manufacturing Example 12-3, except that compound BH-8-2 was used instead of compound BH-6-2 in Manufacturing Example 12-3.

[0525] Manufacturing Example 14-4) Synthesis of compound BH-8-4

[0526] Compound BH-8-4 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that intermediate F and compound BH-8-3 were used instead of SM1 and SM2 in Manufacturing Example 1-1.

[0527] Manufacturing Example 14-5) Synthesis of compound BH-8

[0528] Compound BH-8 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-8-4 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0529] Manufacturing Example 15. Synthesis of Compound BH-9

[0530]

[0531] Manufacturing Example 15-1) Synthesis of compound BH-9-1

[0532] Compound BH-9-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-2, except that 5-chloronaphtho[1,2-b]furan was used instead of intermediate A-1 in Manufacturing Example 1-2.

[0533] Manufacturing Example 15-2) Synthesis of compound BH-9-2

[0534] Compound BH-9-2 was obtained by synthesizing in the same manner as in Manufacturing Example 13-1, except that 1,6-dibromopyrene and compound BH-9-1 were used instead of 1,8-dibromopyrene and intermediate E in Manufacturing Example 13-1.

[0535] Manufacturing Example 15-3) Synthesis of compound BH-9

[0536] Compound BH-9 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-9-2 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0537] Manufacturing Example 16. Synthesis of Compound BH-10

[0538]

[0539] Manufacturing Example 16-1) Synthesis of compound BH-10-1

[0540] Compound BH-10-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0541] Manufacturing Example 16-2) Synthesis of compound BH-10-2

[0542] Compound BH-10-1 (1 eq) and intermediate B (1.1 eq) were added to 1,4-dioxane (10 times the amount of compound BH-10-1), then 2 M potassium phosphate aqueous solution (30% volume ratio compared to 1,4-dioxane) was added, and bis(tri-tertbutylphostin)palladium(0) (1 mol%) was added, followed by heating and stirring for 10 hours. After lowering the temperature to room temperature and completing the reaction, the potassium phosphate aqueous solution was separated and removed, and 1,4-dioxane was distilled under reduced pressure. After dissolving it in chloroform, it was placed in a separatory funnel, washed three times with distilled water, and the organic layer was dried over anhydrous magnesium sulfate. Afterwards, the chloroform was removed by reducing the pressure and recrystallized with EA (Etyl Acetate) to obtain compound BH-10-2 in a solid state.

[0543] Manufacturing Example 16-3) Synthesis of compound BH-10

[0544] Compound BH-10 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-10-2 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0545] Manufacturing Example 17. Synthesis of Compound BH-11

[0546]

[0547] Manufacturing Example 17-1) Synthesis of compound BH-11-1

[0548] Compound BH-11-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1 and SM2 were changed as in the reaction formula.

[0549] Manufacturing Example 17-2) Synthesis of compound BH-11-2

[0550] Compound BH-11-2 was obtained by synthesizing in the same manner as in Manufacturing Example 16-2, except that compound BH-11-1 and intermediate D were used instead of compound BH-10-1 and intermediate B in Manufacturing Example 16-2.

[0551] Manufacturing Example 17-3) Synthesis of compound BH-11

[0552] Compound BH-11 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-11-2 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0553] Manufacturing Example 18. Synthesis of Compound BH-12

[0554]

[0555] Manufacturing Example 18-1) Synthesis of compound BH-12-1

[0556] Compound BH-12-1 was obtained by synthesizing in the same manner as in Manufacturing Example 13-1, except that 4,10-dibromopyrene and intermediate B were used instead of 1,8-dibromopyrene and intermediate E in Manufacturing Example 13-1.

[0557] Manufacturing Example 18-2) Synthesis of compound BH-12

[0558] Compound BH-12 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-12-1 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0559] Manufacturing Example 19. Synthesis of Compound BH-13

[0560]

[0561] Manufacturing Example 19-1) Synthesis of compound BH-13-1

[0562] Compound BH-13-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-2, except that compound 4-chloronaphtho[2,3-b]furan was used instead of intermediate A-1 in Manufacturing Example 1-2.

[0563] Manufacturing Example 19-2) Synthesis of compound BH-13-2

[0564] Compound BH-13-2 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that compound BH-13-1 and 1-bromo-2-chlorobenzene were used instead of SM1 and SM2 in Manufacturing Example 1-1.

[0565] Manufacturing Example 19-3) Synthesis of compound BH-13-3

[0566] Compound BH-13-3 was obtained by synthesizing in the same manner as in Manufacturing Example 1-2, except that compound BH-13-2 was used instead of intermediate A-1 in Manufacturing Example 1-2.

[0567] Manufacturing Example 19-4) Synthesis of compound BH-13-4

[0568] Compound BH-13-4 was obtained by synthesizing in the same manner as in Manufacturing Example 13-1, except that 2,7-dibromopyrene and compound BH-13-3 were used instead of 1,8-dibromopyrene and intermediate E in Manufacturing Example 13-1.

[0569] Manufacturing Example 19-5) Synthesis of compound BH-13

[0570] Compound BH-13 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-13-4 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0571] Manufacturing Example 20. Synthesis of Compound BH-14

[0572]

[0573] Manufacturing Example 20-1) Synthesis of compound BH-14-1

[0574] Compound BH-14-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that 1-bromo-6-chloropyrene and intermediate E were used instead of SM1 and SM2 in Manufacturing Example 1-1.

[0575] Manufacturing Example 20-2) Synthesis of compound BH-14-2

[0576] Compound BH-14-2 was obtained by synthesizing in the same manner as in Manufacturing Example 16-2, except that compound BH-14-1 was used instead of compound BH-10-1 in Manufacturing Example 16-2.

[0577] Manufacturing Example 20-3) Synthesis of compound BH-14

[0578] Compound BH-14 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-14-2 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0579] Manufacturing Example 21. Synthesis of Compound BH-15

[0580]

[0581] Manufacturing Example 21-1) Synthesis of compound BH-15-1

[0582] Compound BH-15-1 was obtained by synthesizing in the same manner as in Manufacturing Example 1-1, except that SM1-1 and intermediate F were used instead of SM1 and SM2 in Manufacturing Example 1-1.

[0583] Manufacturing Example 21-2) Synthesis of compound BH-15-2

[0584] Compound BH-15-2 was obtained by synthesizing in the same manner as in Manufacturing Example 13-1, except that compound BH-15-1 and phenylboronic acid were used instead of 1,8-dibromopyrene and intermediate E in Manufacturing Example 13-1.

[0585] Manufacturing Example 21-3) Synthesis of compound BH-15

[0586] Compound BH-15 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-15-2 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0587] Manufacturing Example 22. Synthesis of Compound BH-16

[0588]

[0589] Manufacturing Example 22-1) Synthesis of compound BH-16-1

[0590] Compound BH-16-1 was obtained by synthesizing in the same manner as in Manufacturing Example 13-1, except that SM1 and SM2 were changed as in the reaction formula.

[0591] Manufacturing Example 22-2) Synthesis of compound BH-16-2

[0592] Compound BH-16-1 (1 eq) and phenylboronic acid (2.2 eq) were added to 1,4-dioxane (10 times that of compound BH-16-1), then 2 M potassium phosphate aqueous solution (30% volume ratio compared to 1,4-dioxane) was added, and bis(tri-tertbutylphostin)palladium(0) (1 mol%) was added, followed by heating and stirring for 10 hours. After lowering the temperature to room temperature and completing the reaction, the potassium phosphate aqueous solution was separated and removed, and 1,4-dioxane was distilled under reduced pressure. After dissolving it in chloroform, it was placed in a separatory funnel, washed three times with distilled water, and the organic layer was dried over anhydrous magnesium sulfate. Afterwards, the chloroform was removed by reducing the pressure and recrystallized with EA (Etyl Acetate) to obtain compound BH-16-2 in a solid state.

[0593] Manufacturing Example 22-3) Synthesis of compound BH-16

[0594] Compound BH-16 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-16-2 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0595] Manufacturing Example 23. Synthesis of Compound BH-17

[0596]

[0597] Manufacturing Example 23-1) Synthesis of compound BH-17-1

[0598] 1,3,6,8-Tetrabromopyrene (1 eq) and intermediate C (4.4 eq) were added to tetrahydrofuran (THF, 20 times the amount of 1,3,6,8-tetrabromopyrene), followed by addition of 8 M potassium carbonate aqueous solution (30% volume ratio compared to THF), followed by addition of tetrakistriphenyl-phosphinopalladium (8 mol%), and heated and stirred for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was separated and removed, and THF was distilled under reduced pressure. After dissolving in chloroform, the mixture was placed in a separatory funnel, washed three times with distilled water, and the organic layer was dried over anhydrous magnesium sulfate. Afterwards, chloroform was removed under reduced pressure, and recrystallized from toluene to obtain compound BH-17-1 in a solid state.

[0599] Manufacturing Example 23-2) Synthesis of compound BH-17

[0600] Compound BH-17 was prepared by synthesizing in the same manner as in Manufacturing Example 7-2, except that compound BH-17-1 was used instead of compound BH-1-1 in Manufacturing Example 7-2.

[0601] <Example>

[0602] Example 1.

[0603] The substrate on which ITO (Indium tin oxide) / Ag / ITO was deposited at 70Å / 1000Å / 70Å as an anode was cut into 50mm x 50mm x 0.5mm sizes, placed in distilled water containing a dispersant, and ultrasonically cleaned. The detergent was a product of Fischer Co., and the distilled water was distilled water that had been secondarily filtered through a filter of Millipore Co. After washing the ITO for 30 minutes, it was ultrasonically cleaned twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonically cleaned in the order of isopropyl alcohol, acetone, and methanol, and then dried.

[0604] On the ITO transparent electrode thus prepared, the following HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer. Subsequently, HTL-1 was thermally vacuum deposited to a thickness of 100 nm, and then HTL-2 was thermally vacuum deposited to a thickness of 10 nm to form a hole transport layer. Subsequently, the compound BH-2 (host 1) synthesized in the above manufacturing example and the compound BD-1 (dopant) below (host 1 compound weight ratio: dopant compound weight ratio = 95:5) were simultaneously vacuum deposited to form a first light-emitting layer having a thickness of 85 Å. Subsequently, the compound BH-A (host 2) below and the compound BD-1 (dopant) below (host 2 compound weight ratio: dopant compound weight ratio = 95:5) were simultaneously vacuum deposited to form a second light-emitting layer having a thickness of 85 Å. Next, ETL2 was deposited to a thickness of 50 Å to form an electron control layer, and compound ETL1 and lithium quinolate (Liq) were mixed in a ratio of 7:3 to form an electron transport layer with a thickness of 250 Å. Sequentially, magnesium and lithium fluoride (LiF) with a thickness of 50 Å were deposited as an electron injection layer.

[0605] After forming a 200Å cathode with magnesium and silver (1:4), CP1 was deposited to complete the device. During the above process, the deposition rate of the organic material was maintained at 1Å / sec.

[0606]

[0607]

[0608] Examples 2 to 32 and Comparative Examples 1 to 3.

[0609] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds described in Table 1 below were used as host 1, host 2, and dopant, respectively.

[0610] At this time, among the hosts described in Table 1, the compounds represented by the chemical formula 1 of the present invention (compounds BH-2 to BH-17) were manufactured through the same process as Manufacturing Examples 8 to 23 described above.

[0611] BH-C, BH-K, and BH-L used in Comparative Examples 1 to 3 are as follows, respectively.

[0612]

[0613] 10 mA / cm for the organic light-emitting devices manufactured in Examples 1 to 32 and Comparative Examples 1 to 10 2 The driving voltage (Voc) and luminous efficiency (cd / A) were measured at a current density of 20 mA / cm 2 The time (LT) for the initial luminance to reach 95% of the current density was measured, and the results are shown in Table 1 below.

[0614] No. Host 1 Host 2 Dopant 10 mA / cm 2Measurement value LT (T95%) VocCd / A Example 1 BH-2BH-ABD-23.45 6.48 213 Example 2 BH-3BH-ABD-13.49 6.52 221 Example 3 BH-4BH-ABD-23.5 16.58 208 Example 4 BH-5BH-ABD-13.48 6.49 209 Example 5 BH-6BH-ABD-23.42 6.50 220 Example 6 BH-7BH-ABD-13.5 0 6.44 212 Example 7 BH-8BH-ABD-23.49 6.56 209 Example 8 BH-9BH-ABD-13.41 6.53 215 Example 9BH-10BH-ABD-23.416.51210 Example 10BH-11BH-ABD-13.466.45218 Example 11BH-12BH-ABD-23.396.48223 Example 12BH-13BH-ABD-13.456.51223 Example 13BH-14BH-ABD-23.496.50217 Example 14BH-15BH-ABD-13.456.47212 Example 15BH-16BH-ABD-23.506.50225 Example 16BH-17BH-ABD-13.516.48213 Example 17BH-2BH-BBD-13.486.48211 Example 18BH-3BH-BBD-23.436.52210 Example 19BH-4BH-BBD-13.426.44214 Example 20BH-5BH-BBD-23.496.50218 Example 21BH-6BH-BBD-13.466.51213 Example 22BH-7BH-BBD-23.506.49218 Example 23BH-8BH-BBD-13.446.53222 Example 24BH-9BH-BBD-23.486.48223 Example 25BH-10BH-BBD-13.446.47220Example 26BH-11BH-BBD-23.466.46219Example 27BH-12BH-BBD-13.476.50215Example 28BH-13BH-BBD-23.456.53216Example 29BH-14BH-BBD-13.476.45217Example 30BH-15BH-BBD-23.466.44220Example 31BH-16BH-BBD-13.406.43223Example 32BH-17BH-BBD-23.406.46218Comparative Example 1BH-CBH-ABD-13.656.2087Comparative example 2BH-KBH-ABD-23.786.0287Comparative example 3BH-LBH-BBD-13.855.9893.

[0615] As shown in Table 1 above, the organic light-emitting device in which the compound of the present invention was applied to the light-emitting layer exhibited excellent lifespan characteristics.

[0616] On the other hand, organic light-emitting devices that used compounds other than chemical formula 1 in the light-emitting layer showed characteristics of reduced lifespan.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, One to four of R2 to R5 and R7 to R10 are bonded to the following chemical formula 2, The remaining R2 to R5 and R7 to R10 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, R1 and R6 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, [Chemical formula 2] In the above chemical formula 2, X is O or S, A1, A2 and R11 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, l1 is an integer from 1 to 4, and if l1 is 2 or greater, two or more L1s are equal to or different from each other. r11 is an integer from 1 to 5, and when r11 is 2, 2 or more R11s are equal to or different from each other, * is a part that is bonded to the above chemical formula 1.

2. In claim 1, the chemical formula 2 is a compound which is any one of the following chemical formulas 2-1 to 2-3: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] In the above chemical formulas 2-1 to 2-3, X is O or S, L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, A1, A2, R12 and R13 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, l1 is an integer from 1 to 4, and if l1 is 2 or greater, two or more L1s are equal to or different from each other. r12 is 1 or 2, r13 is an integer from 1 to 4, r12+r13 is an integer from 1 to 5, and when r12 and r13 are 2 or greater, the substituents in each parenthesis are the same or different, * is a part that is bonded to the above chemical formula 1.

3. In claim 1, the chemical formula 1 is a compound having the following chemical formula 1-1 or 1-2: In the above chemical formulas 1-1 and 1-2, R1 to R10 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, is a part that combines with the above chemical formula 2.

4. In claim 1, the chemical formula 1 is a compound which is any one of the following chemical formulas 1-11 to 1-20: In the above chemical formulas 1-11 to 1-20, R1 to R10 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, is a part that combines with the above chemical formula 2.

5. In claim 1, the chemical formula 1 is a compound which is any one of the following chemical formulas 1-31 to 1-35: In the above chemical formulas 1-31 to 1-35, R1 and R3 to R10 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, is a part that combines with the above chemical formula 2.

6. In claim 1, one to four of R2 to R5 and R7 to R10 are combined with the chemical formula 2, A compound wherein the remaining R2 to R5 and R7 to R10 are the same as or different from each other, and each independently represents hydrogen; deuterium; 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 phenanthrene group; a substituted or unsubstituted benzophenanthrene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

7. A compound according to claim 1, wherein R1 and R6 are the same as or different from each other, and are each independently hydrogen; deuterium; 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 phenanthrene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

8. A compound according to claim 1, wherein A1 and A2 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted aryl group.

9. In claim 1, the compound is a compound having any one of the following structures: .

10. First electrode; a second electrode; and An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode, An organic light-emitting device, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 9.

11. An organic light-emitting device according to claim 10, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

12. An organic light-emitting device according to claim 10, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

13. In claim 11, the light-emitting layer comprises a host and a dopant, The above host comprises the above compound, An organic light-emitting device wherein the dopant comprises at least one compound selected from the following chemical formulas D, E and F: [Chemical Formula D] [Chemical formula E] [Chemical formula F] In the above chemical formulas D, E and F, Y1 to Y4 are the same as or different from each other, and are each independently CR' or NR", and at least one of Y1 and Y2 and at least one of Y3 and Y4 is NR", Z1 to Z4 are the same as or different from each other, and each independently represents a substituted or unsubstituted 5-membered ring; a substituted or unsubstituted 6-membered ring; or a condensed ring of a substituted or unsubstituted 5-membered ring and a 6-membered ring, R401, R402, R' and R" are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or are bonded to adjacent groups to form a substituted or unsubstituted ring, Lx is a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group, provided that Lx is not a divalent pyrene group; Ar101 to Ar104 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, r401 and r402 are each an integer from 1 to 3, and when r401 and r402 are 2 or greater, the substituents in each parenthesis are the same or different.

14. In claim 11, the organic light-emitting device wherein the light-emitting layer comprises the compound as a first host and further comprises a second host of the following chemical formula H: [chemical formula H] In the above chemical formula H, R100 to R109 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

15. In claim 11, the light-emitting layer comprises a first light-emitting layer provided between the first electrode and the second electrode; and a second light-emitting layer provided between the first light-emitting layer and the second electrode and in contact with the first light-emitting layer. An organic light-emitting device, wherein either one of the first light-emitting layer and the second light-emitting layer comprises the compound.

16. An organic light-emitting device according to claim 15, wherein the first light-emitting layer comprises the compound, and the second light-emitting layer comprises a compound of the following chemical formula H: [chemical formula H] In the above chemical formula H, R100 to R109 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

17. An organic light-emitting device according to claim 15, wherein the first light-emitting layer comprises two or more hosts, and one of the two or more hosts is the compound.

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