Compound and organic light-emitting element comprising same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device comprising the same. Specifically, the compound includes pyrene substituted with a naphthofuryl group or a naphthothienyl group, and the organic light-emitting device includes: a first electrode; a second electrode; and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound described above.

Description

Technical Field

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

[0003] Organic light emission (OLED) typically refers to the phenomenon where electrical energy is converted into light energy using organic materials. Organic light-emitting devices (OLEDs) utilizing this phenomenon generally have a structure comprising an anode, a cathode, and an organic material layer between them. This organic material layer typically has a multilayer structure composed of different materials to improve the efficiency and stability of the OLED. For example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of an OLED, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons recombine, excitons are formed, and light is emitted when the excitons return to the ground state.

[0004] New materials need to be developed for organic light-emitting devices. Summary of the Invention

[0005] Technical issues

[0006] This specification provides compounds and organic light-emitting devices containing them.

[0007] Technical solution

[0008] An exemplary embodiment of this specification provides a compound of chemical formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In chemical formula 1,

[0012] One to four of R2 to R5 and R7 to R10 are bonded to chemical formula 2.

[0013] The remaining R2 to R5 and R7 to R10 may be the same or different, and are each independently hydrogen; deuterium; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, and

[0014] R1 and R6 may be the same or different, and each is independently hydrogen; deuterium; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0015] [Chemical Formula 2]

[0016]

[0017] In chemical formula 2,

[0018] X is O or S.

[0019] A1, A2, and R11 may be the same or different, and each is independently hydrogen; deuterium; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0020] L1 is a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0021] l1 is an integer from 1 to 4, and if l1 is 2 or greater, then two or more L1 values ​​are the same or different.

[0022] r11 is an integer from 1 to 5, and if r11 is 2 or greater, then two or more R11 values ​​are the same or different.

[0023] This refers to the portion that is bonded to chemical formula 1.

[0024] Another exemplary embodiment of this specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more layers of organic material disposed between the first electrode and the second electrode, wherein one or more layers of organic material contain the aforementioned compound.

[0025] Beneficial effects

[0026] The compound according to an exemplary embodiment of this specification can be used in organic light-emitting devices (OLEDs) to reduce the driving voltage and improve the efficiency of the OLEDs. Furthermore, the thermal stability of the compound can improve the lifetime characteristics of the device. Attached Figure Description

[0027] Figures 1 to 5 Examples of organic light-emitting devices according to some exemplary embodiments of this specification are shown.

[0028] Figure 6 The MS spectrum of compound A is shown below.

[0029] [Detailed Description of Key Components]

[0030] 1: Base

[0031] 2: First electrode

[0032] 3: Second electrode

[0033] 4: Emissive layer

[0034] 4-1: First light-emitting layer

[0035] 4-2: Second light-emitting layer

[0036] 5: Hole injection layer

[0037] 6: Hole transport layer

[0038] 6-1: First Hole Transport Layer

[0039] 6-2: Second Hole Transport Layer

[0040] 7: Electronic Control Layer

[0041] 8: Electron transport layer

[0042] 9: Electron injection layer

[0043] 10: Organic material layer Detailed Implementation

[0044] An exemplary embodiment of this specification provides a compound of chemical formula 1.

[0045] According to an exemplary embodiment of this specification, the compound of Formula 1 is a pyrene-based compound substituted with Formula 2. By including Formula 2, the injection, transport, and control properties of holes and electrons can be improved.

[0046] The terminology used in this specification is explained in more detail below to aid understanding.

[0047] In this disclosure, when a component is “included” in a part of this specification, it does not mean that other components are excluded, but rather that other components may be included, unless otherwise specifically described.

[0048] In this disclosure, when one component (layer) is disposed "on" another component (layer) in the present invention, this includes not only the case where one component (layer) is in contact with the other component, but also the case where there is another component (layer) between the two components (layers).

[0049] In this invention, "layer" has the same meaning as "film" commonly used in the art, and refers to a coating covering a target area. The size of a "layer" is not limited, and the sizes of individual "layers" can be the same or different from each other. In one exemplary embodiment, the size of a "layer" can be the same as the size of the entire device, can correspond to the size of a specific functional area, and can also be as small as a single subpixel.

[0050] In this specification, "or" means inclusive "or" rather than exclusive "or". For example, if conditions A or B are satisfied, it means that 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), or both A and B are true (or exist).

[0051] In this specification, the meaning of "a specific material A is contained in layer B" includes i) one or more materials A are contained in a layer B, and ii) layer B consists of one or more layers, and material A is contained in one or more of the plurality of layers B.

[0052] In this specification, the description of a particular material A being contained in layer C or layer D means that material A i) is contained in at least one of one or more layers C, ii) is contained in at least one of one or more layers D, or iii) is contained in one or more layers C and one or more layers D.

[0053] In this specification, " "and" "" refers to the portion connected to each substituent or binding moiety.

[0054] The term "substitution" refers to the replacement of a hydrogen atom bonded to a carbon atom in a compound by another substituent. There are no restrictions on the position of the substitution, as long as it is a position where the hydrogen atom can be substituted. When two or more substituents are present, they can be the same or different.

[0055] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from: deuterium; halogen group; nitrile (-CN); nitro; hydroxyl; alkyl; cycloalkyl; alkoxy; phosphine oxide; aryloxy; alkylthio; arylthio; alkylsulfonyl; arylsulfonyl; alkenyl; silyl; boron; amino; aryl; or heterocyclic, substituted with a substituent formed when two or more of the above substituents are linked, or without any substituents at all. For example, "a substituent linked with two or more substituents" can be biphenyl. That is, biphenyl can be considered as an aryl group, or a substituent linked with two phenyl groups.

[0056] In this specification, the term "substituted or unsubstituted" means substituted with one or more of the following substituents: deuterium; halogen group; nitrile group; silyl group; alkoxy group; aryl group; alkyl group; aryl group; and heterocyclic group, substituted with a substituent formed when two or more of the above substituents are linked together, or has no substituents at all.

[0057] In this specification, the term "substituted or unsubstituted" means substituted with one or more of the following substituents: deuterium; alkyl; aryl; and heterocyclic, substituted with a substituent formed when two or more of the above substituents are linked together, or has no substituents at all.

[0058] In this specification, the description of two or more substituents being linked means that the hydrogen of one substituent is linked to another substituent. For example, phenyl and naphthyl groups can be linked to form... or Furthermore, the connection of the three substituents includes not only the sequential connection of (substituent 1)-(substituent 2)-(substituent 3), but also the connection of (substituent 2) and (substituent 3) with (substituent 1). For example, phenyl, naphthyl, and isopropyl can be linked to form , or The above limitations also apply to cases where four or more substituents are connected.

[0059] Examples of the above substituents are described below, but are not limited to these.

[0060] Examples of halogen groups in this disclosure include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0061] In this disclosure, the silane group can be of the chemical formula -SiY a Y b Y c It means that Y a Y b and Y c Each can be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. There is no particular limitation on the number of carbon atoms in the silane, but it can specifically be 1 to 30, or 3 to 30. Examples of silanes include, but are not limited to, trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc.

[0062] In this specification, the boron group can be represented by the chemical formula -BY d Y e It means that Y d and Ye Each can be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Examples of boron groups include, but are not limited to, dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, phenylboryl, etc.

[0063] In this specification, alkyl groups can be straight-chain or branched. The number of carbon atoms in an alkyl group can specifically be from 1 to 60, but is not particularly limited thereto. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, and n-octyl.

[0064] In this specification, alkoxy groups can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group can specifically be from 1 to 20, but is not particularly limited thereto. Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, etc.

[0065] The alkyl, alkoxy, and other substituents comprising an alkyl moiety described in this disclosure cover both straight-chain and branched forms.

[0066] In this specification, the alkenyl group can be straight-chain or branched. The number of carbon atoms in the alkenyl group can specifically be from 2 to 40, but is not particularly limited thereto. Examples of alkenyl groups include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, It includes, but is not limited to, styrene, etc.

[0067] In this specification, the number of carbon atoms in a cycloalkyl group may specifically be 3 to 30, but is not particularly limited thereto. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]octyl, norbornyl, etc.

[0068] In this disclosure, the amino group refers to -NH2. The amino group can be substituted with alkyl, aryl, heterocyclic, alkenyl, cycloalkyl, or combinations thereof. The number of carbon atoms in the amino group can specifically be from 1 to 30, but is not particularly limited thereto. Examples of amino groups include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthracene amino, dibenzofuranylphenylamino, 9-methylanthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, diphenylamino, etc.

[0069] In this specification, the number of carbon atoms in the aryl group may specifically be 6 to 60, but is not particularly limited thereto. Furthermore, the aryl group may be a monocyclic aryl or a polycyclic aryl. Examples of monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, and tetraphenyl. Examples of polycyclic aryl groups include naphthyl, anthraceneyl, phenanthrene, benzo[a]phenanthreneyl, pyrene, etc. It includes, but is not limited to, methyl, fluorene, triphenylene, etc.

[0070] In this disclosure, the fluorene group may be substituted, and two substituents may combine to form a spirocyclic structure.

[0071] When the fluorene group is substituted, it can be a spirofluorene group, for example... , etc., or substituted fluorene groups, for example (9,9-dimethylfluorenyl) and (9,9-diphenylfluorene), but not limited to this.

[0072] In this specification, the foregoing description of aryl applies to aryl groups in the aryloxy group.

[0073] In this specification, a heterocyclic group is a cyclic group containing at least one of N, O, P, S, Si, and Se as a heteroatom. The number of carbon atoms in the heterocyclic group can specifically be from 2 to 60, but is not particularly limited thereto. Examples of heterocyclic groups include, but are not limited to, pyridinyl, pyrroloyl, pyrimidinyl, quinolinyl, pyridazinyl, furanyl, thiopheneyl, imidazoyl, pyrazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, naphthobenzofuranyl, benzonaphthothiopheneyl, indocarbazoleyl, triazinyl, etc.

[0074] In this disclosure, the foregoing description of heterocyclic groups applies to heteroaryl groups, except that heteroaryl groups are aromatic.

[0075] In this specification, in a ring formed by bonding of adjacent groups, "ring" means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0076] In this specification, hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings.

[0077] In this specification, an aliphatic hydrocarbon ring refers to a non-aromatic ring consisting only of carbon and hydrogen atoms. The number of carbon atoms in an aliphatic hydrocarbon ring can specifically be from 3 to 60, but is not particularly limited thereto. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc.

[0078] In this disclosure, an aromatic hydrocarbon ring refers to an aromatic ring composed solely of carbon and hydrogen atoms. The number of carbon atoms in an aromatic hydrocarbon ring can specifically be from 6 to 60, but is not particularly limited thereto. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, etc. fluoranthene, triphenylene, phenaene, pyrene, benzo[a]tetraphenyl It includes, but is not limited to, pentane, fluorene, indene, acenaphthene, benzo[a]fluorene, spirofluorene, etc.

[0079] In this specification, aromatic hydrocarbon cyclic groups can be interpreted as having the same meaning as aryl groups.

[0080] In this specification, arylene means a divalent aryl group having two bonding sites. The foregoing description of aryl groups can be applied, except that arylene is divalent.

[0081] According to this specification, a heteroaryl group refers to a divalent heteroaryl group having two binding sites. The foregoing description applies to heteroaryl groups, except that the heteroaryl group is divalent.

[0082] In this specification, D refers to deuterium.

[0083] In this instruction manual, This means that the structure within the parentheses contains x1 to x2 deuteriums. For example, This indicates that the structure contains 0 to 16 deuterium. For example, the following structure contains 0 to 16 deuterium.

[0084]

[0085] Unless otherwise specified in this specification, 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 disclosure pertains. While similar or equivalent methods and materials to those described herein may be used in the practice or testing of exemplary embodiments of this disclosure, suitable methods and materials will be described below. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, this specification (including limitations) shall prevail unless a specific paragraph is cited. Furthermore, the materials, methods, and examples described are illustrative only and are not intended to be restrictive.

[0086] The compounds of chemical formula 1 will be described in detail below.

[0087] In one exemplary embodiment of this specification, one of R2 to R5 and R7 to R10 is bonded to chemical formula 2.

[0088] In one exemplary embodiment of this specification, chemical formula 1 is chemical formula 1-1 or chemical formula 1-2.

[0089]

[0090] In chemical formulas 1-1 and 1-2,

[0091] R1 to R10 may be the same or different, and each is independently hydrogen; deuterium; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, and

[0092] This refers to the portion that is bonded to chemical formula 2.

[0093] In one exemplary embodiment of this specification, two of R2 to R5 and R7 to R10 are bonded to chemical formula 2.

[0094] In one exemplary embodiment of this specification, chemical formula 1 is any one of chemical formulas 1-11 to 1-20.

[0095]

[0096]

[0097] In chemical formulas 1-11 to 1-20,

[0098] R1 to R10 may be the same or different, and each is independently hydrogen; deuterium; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, and

[0099] This refers to the portion that is bonded to chemical formula 2.

[0100] In one exemplary embodiment of this specification, three of R2 to R5 and R7 to R10 are bonded to chemical formula 2.

[0101] In one exemplary embodiment of this specification, four of R2 to R5 and R7 to R10 are bonded to chemical formula 2.

[0102] In one exemplary embodiment of this specification, chemical formula 1 is any one of chemical formulas 1-31 to 1-35.

[0103]

[0104] In chemical formulas 1-31 to 1-35

[0105] R1 and R3 through R10 may be the same or different, each being independently hydrogen; deuterium; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, and

[0106] This refers to the portion that is bonded to chemical formula 2.

[0107] In one exemplary embodiment of this specification, one to four of R2 to R5 and R7 to R10 are bonded to Formula 2, and the remaining R2 to R5 and R7 to R10 are the same or different, each being independently hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic.

[0108] In other words, the remainder of R2 to R5 and R7 to R10 that are not bonded to Formula 2 are the same or different, and are each independently hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic.

[0109] For example, R2 is bonded to Formula 2, and the remainder of R3 to R5 and R7 to R10 are the same or different, each being independently hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic.

[0110] In one exemplary embodiment of this specification, one to four of R2 to R5 and R7 to R10 are bonded to Formula 2, and the remaining R2 to R5 and R7 to R10 are the same or different, each being 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.

[0111] In one exemplary embodiment of this specification, one to four of R2 to R5 and R7 to R10 are bonded to Formula 2, and the remaining R2 to R5 and R7 to R10 are the same or different, each being 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.

[0112] In one exemplary embodiment of this specification, one to four of R2 to R5 and R7 to R10 are bonded to Formula 2, and the remaining R2 to R5 and R7 to R10 are the same or different, each being independently hydrogen; deuterium; an aryl group substituted or unsubstituted with one or more of deuterium, alkyl, aryl and heterocyclic groups; or a heterocyclic group substituted or unsubstituted with one or more of deuterium, alkyl, aryl and heterocyclic groups.

[0113] In one exemplary embodiment of this specification, one to four of R2 to R5 and R7 to R10 are bonded to Formula 2, and the remaining R2 to R5 and R7 to R10 are the same or different, each being independently hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthyl; substituted or unsubstituted benzophenanthryl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiopheneyl.

[0114] In one exemplary embodiment of this specification, one to four of R2 to R5 and R7 to R10 are bonded to Formula 2, and the remaining R2 to R5 and R7 to R10 may be the same or different, each being independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with one or more of deuterium, alkyl, aryl, and heterocyclic groups; a biphenyl group substituted or unsubstituted with one or more of deuterium, alkyl, aryl, and heterocyclic groups; or a terphenyl group substituted or unsubstituted with one or more of deuterium, alkyl, aryl, and heterocyclic groups. Naphthyl group; naphthyl group substituted or unsubstituted with one or more of deuterium, alkyl, aryl and heterocyclic groups; phenanthryl group substituted or unsubstituted with one or more of deuterium, alkyl, aryl and heterocyclic groups; benzophenanthryl group substituted or unsubstituted with one or more of deuterium, alkyl, aryl and heterocyclic groups; dibenzofuranyl group substituted or unsubstituted with one or more of deuterium, alkyl, aryl and heterocyclic groups; or dibenzothiophenyl group substituted or unsubstituted with one or more of deuterium, alkyl, aryl and heterocyclic groups.

[0115] In one exemplary embodiment of this specification, one to four of R2 to R5 and R7 to R10 are bonded to Formula 2, and the remaining R2 to R5 and R7 to R10 may be the same or different, each being independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with one or more of deuterium, aryl, and heterocyclic groups; a biphenyl group substituted or unsubstituted with one or more of deuterium, aryl, and heterocyclic groups; a phenyl group substituted or unsubstituted with one or more of deuterium, aryl, and heterocyclic groups. Triphenyl; naphthyl group substituted or unsubstituted with one or more of deuterium, aryl, and heterocyclic groups; phenanthryl group substituted or unsubstituted with one or more of deuterium, aryl, and heterocyclic groups; benzophenanthryl group substituted or unsubstituted with one or more of deuterium, aryl, and heterocyclic groups; dibenzofuranyl group substituted or unsubstituted with one or more of deuterium, aryl, and heterocyclic groups; or dibenzothiophenyl group substituted or unsubstituted with one or more of deuterium, aryl, and heterocyclic groups.

[0116] In one exemplary embodiment of this specification, one to four of R2 to R5 and R7 to R10 are bonded to Formula 2, and the remaining R2 to R5 and R7 to R10 are the same or different, each being independently hydrogen; deuterium; a phenyl group substituted or unsubstituted with one or more of deuterium, naphthyl, dibenzofuranyl, and dibenzothiophene; a biphenyl group substituted or unsubstituted with one or more of deuterium, naphthyl, dibenzofuranyl, and dibenzothiophene; and a terphenyl group substituted or unsubstituted with one or more of deuterium, naphthyl, dibenzofuranyl, and dibenzothiophene. Naphthyl group substituted or unsubstituted with one or more of deuterium, phenyl, naphthyl, dibenzofuranyl and dibenzothiopheneyl; phenanthryl group substituted or unsubstituted with one or more of deuterium, phenyl, naphthyl, dibenzofuranyl and dibenzothiopheneyl; benzophenanthryl group substituted or unsubstituted with one or more of deuterium, phenyl, naphthyl, dibenzofuranyl and dibenzothiopheneyl; dibenzofuranyl group substituted or unsubstituted with one or more of deuterium, phenyl and naphthyl; or dibenzothiopheneyl group substituted or unsubstituted with one or more of deuterium, phenyl and naphthyl.

[0117] In one exemplary embodiment of this specification, R1 and R6 may be the same or different, each being independently hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiophenyl.

[0118] In one exemplary embodiment of this specification, R1 and R6 may be the same or different, each being independently hydrogen; deuterium; a phenyl group that is deuterated or unsubstituted; a biphenyl group that is deuterated or unsubstituted; a terphenyl group that is deuterated or unsubstituted; a naphthyl group that is deuterated or unsubstituted; a phenanthryl group that is deuterated or unsubstituted; or a dibenzothiophene group that is deuterated or has deuterium.

[0119] In one exemplary embodiment of this specification, R1 and R6 may be the same or different, each being independently hydrogen or deuterium.

[0120] In one exemplary embodiment of this specification, A1 and A2 may be the same or different, each being independently 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.

[0121] In one exemplary embodiment of this specification, A1 and A2 may be the same or different, each being independently hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0122] In one exemplary embodiment of this specification, A1 and A2 may be the same or different, each being independently hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; or substituted or unsubstituted naphthyl.

[0123] In one exemplary embodiment of this specification, chemical formula 2 is any one of chemical formulas 2-1 to 2-3.

[0124] [Chemical Formula 2-1]

[0125]

[0126] [Chemical Formula 2-2]

[0127]

[0128] [Chemical Formula 2-3]

[0129]

[0130] In chemical formulas 2-1 to 2-3

[0131] X is O or S.

[0132] L1 is a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0133] A1, A2, R12, and R13 may be the same or different, and each is independently hydrogen; deuterium; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0134] l1 is an integer from 1 to 4, and if l1 is 2 or greater, then two or more L1 values ​​are the same or different.

[0135] 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 parentheses are the same or different, and

[0136] This refers to the portion that is bonded to chemical formula 1.

[0137] In one exemplary embodiment of this specification, chemical formula 2-1 is any one of chemical formulas 2-1-1 to 2-1-6.

[0138] [Chemical Formula 2-1-1]

[0139]

[0140] [Chemical Formula 2-1-2]

[0141]

[0142] [Chemical Formula 2-1-3]

[0143]

[0144] [Chemical Formula 2-1-4]

[0145]

[0146] [Chemical Formula 2-1-5]

[0147]

[0148] [Chemical Formula 2-1-6]

[0149]

[0150] In chemical formulas 2-1-1 to 2-1-6,

[0151] X, L1, A1, A2, and l1 are the same as those defined in chemical formula 2.

[0152] R12 and R13 may be the same or different, and each is independently hydrogen; deuterium; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0153] r12 is either 1 or 2, and when r12 is 2, the substituents in parentheses are either the same or different.

[0154] r13' is an integer from 1 to 3, r13 is an integer from 1 to 4, and when r13 and r13' are 2 or greater, the substituents in parentheses are the same or different, and

[0155] This refers to the portion that is bonded to chemical formula 1.

[0156] In one exemplary embodiment of this specification, chemical formula 2-2 is any one of chemical formulas 2-2-1 to 2-2-6.

[0157] [Chemical Formula 2-2-1]

[0158]

[0159] [Chemical Formula 2-2-2]

[0160]

[0161] [Chemical Formula 2-2-3]

[0162]

[0163] [Chemical Formula 2-2-4]

[0164]

[0165] [Chemical Formula 2-2-5]

[0166]

[0167] [Chemical Formula 2-2-6]

[0168]

[0169] In chemical formulas 2-2-1 to 2-2-6

[0170] X, L1, A1, A2, and l1 are the same as those defined in chemical formula 2.

[0171] R12 and R13 may be the same or different, and each is independently hydrogen; deuterium; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0172] r12 is either 1 or 2, and when r12 is 2, the substituents in parentheses are either the same or different.

[0173] r13' is an integer from 1 to 3, r13 is an integer from 1 to 4, and when r13 and r13' are 2 or greater, the substituents in parentheses are the same or different, and

[0174] This refers to the portion that is bonded to chemical formula 1.

[0175] In one exemplary embodiment of this specification, chemical formula 2-3 is any one of chemical formulas 2-3-1 to 2-3-6.

[0176] [Chemical Formula 2-3-1]

[0177]

[0178] [Chemical Formula 2-3-2]

[0179]

[0180] [Chemical Formula 2-3-3]

[0181]

[0182] [Chemical Formula 2-3-4]

[0183]

[0184] [Chemical Formula 2-3-5]

[0185]

[0186] [Chemical Formula 2-3-6]

[0187]

[0188] In chemical formulas 2-3-1 to 2-3-6

[0189] X, L1, A1, A2, and l1 are the same as those defined in chemical formula 2.

[0190] R12 and R13 may be the same or different, and each is independently hydrogen; deuterium; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0191] r12 is either 1 or 2, and when r12 is 2, the substituents in parentheses are either the same or different.

[0192] r13' is an integer from 1 to 3, r13 is an integer from 1 to 4, and when r13 and r13' are 2 or greater, the substituents in parentheses are the same or different, and

[0193] This refers to the portion that is bonded to chemical formula 1.

[0194] In one exemplary embodiment of this specification, L1 is a direct bond; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0195] In one exemplary embodiment of this specification, L1 is a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted naphthylene; a substituted or unsubstituted divalent dibenzofuranyl; or a substituted or unsubstituted divalent dibenzothiopheneyl.

[0196] In one exemplary embodiment of this specification, L1 is a direct bond; a phenylene group substituted or unsubstituted with one or more of deuterium, alkyl, aryl, and heterocyclic groups; a biphenylene group substituted or unsubstituted with one or more of deuterium, alkyl, aryl, and heterocyclic groups; a naphthylene group substituted or unsubstituted with one or more of deuterium, alkyl, aryl, and heterocyclic groups; a divalent dibenzofuran group substituted or unsubstituted with one or more of deuterium, alkyl, aryl, and heterocyclic groups; or a divalent dibenzothiophene group substituted or unsubstituted with one or more of deuterium, alkyl, aryl, and heterocyclic groups.

[0197] In one exemplary embodiment of this specification, L1 is a direct bond; a phenylene substituted or unsubstituted with one or more of deuterium and aryl groups; a biphenylene substituted or unsubstituted with one or more of deuterium and aryl groups; a naphthylene substituted or unsubstituted with one or more of deuterium and aryl groups; a divalent dibenzofuranyl substituted or unsubstituted with one or more of deuterium and aryl groups; or a divalent dibenzothiopheneyl substituted or unsubstituted with one or more of deuterium and aryl groups.

[0198] In one exemplary embodiment of this specification, L1 is a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted naphthylene; or a substituted or unsubstituted divalent dibenzofuranyl.

[0199] In one exemplary embodiment of this specification, L1 is a direct bond; a phenylene substituted or unsubstituted with one or more of deuterium and aryl groups; a biphenylene substituted or unsubstituted with one or more of deuterium and aryl groups; a naphthylene substituted or unsubstituted with one or more of deuterium and aryl groups; or a divalent dibenzofuranyl substituted or unsubstituted with one or more of deuterium and aryl groups.

[0200] In one exemplary embodiment of this specification, L1 is a direct bond; a deuterated or unsubstituted phenylene; a deuterated or unsubstituted biphenylene; a deuterated or unsubstituted naphthylene; or a deuterated or unsubstituted dibenzofuranyl.

[0201] In one exemplary embodiment of this 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.

[0202] In one exemplary embodiment of this specification, R11 is hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0203] In one exemplary embodiment of this specification, R11 is hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; or substituted or unsubstituted naphthyl.

[0204] In one exemplary embodiment of this specification, R11 is hydrogen; or deuterium.

[0205] In one exemplary embodiment of this specification, R12 and R13 may be the same or different, each being 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.

[0206] In one exemplary embodiment of this specification, R12 and R13 may be the same or different, each being independently hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0207] In one exemplary embodiment of this specification, R12 and R13 may be the same or different, each being independently hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; or substituted or unsubstituted naphthyl.

[0208] In one exemplary embodiment of this specification, R12 and R13 may be the same or different, each being independently hydrogen; or deuterium.

[0209] In one exemplary embodiment of this specification, the compound of formula 1 contains at least one deuterium.

[0210] In one exemplary embodiment of this specification, the deuterium substitution rate of the compound of Formula 1 is 10% or higher.

[0211] In one exemplary embodiment of this specification, the deuterium substitution rate of the compound of Formula 1 is 20% or higher.

[0212] In one exemplary embodiment of this specification, the deuterium substitution rate of the compound of Formula 1 is 30% or higher.

[0213] In one exemplary embodiment of this specification, the deuterium substitution rate of the compound of Formula 1 is 40% or higher.

[0214] In one exemplary embodiment of this specification, there is no upper limit to the deuterium substitution rate of the compound of Formula 1, but it can be, for example, 100% or lower, or less than 100%.

[0215] For example, the deuterium substitution rate of chemical formula 1 is 10% to 100%.

[0216] In this specification, "containing deuterium", "deuterated" or "deuterated" means that hydrogen at a substituted position in the compound is replaced by deuterium.

[0217] In this specification, "fully deuterated" means a compound or group in which all hydrogen atoms in the molecule are replaced by deuterium, and has the same meaning as "100% deuterated".

[0218] In this specification, "X% deuterated", "X% degree of deuteration", or "X% rate of deuteration substitution" means that X% of the hydrogens at the substituted positions in the structure are replaced by deuterium. For example, when the structure is dibenzofuran, "25% deuterated", "25% degree of deuteration", or "25% rate of deuteration substitution" means that two of the eight hydrogens at the substituted positions in the dibenzofuran are replaced by deuterium.

[0219] In this specification, "degree of deuteration" or "deuteration substitution rate" can be determined by known methods such as nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 It is determined by methods such as ¹H NMR, thin-layer chromatography / mass spectrometry (TLC / MS), and gas chromatography / mass spectrometry (GC / MS).

[0220] Specifically, when using nuclear magnetic resonance spectroscopy (NMR spectroscopy) 1 When analyzing "degree of deuteration" or "deuteration substitution rate" using ¹H NMR, the degree of deuteration or deuteration substitution rate can be determined by adding DMF (dimethylformamide) as an internal standard. 1 The calculation is performed using the integrated peak area on the H NMR spectrum.

[0221] Furthermore, when analyzing "degree of deuteration" or "deuteration substitution rate" by TLC / MS (thin-layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum (median) value of the molecular weight distribution at the reaction endpoint. For example, when analyzing the degree of deuteration of compound A, if the starting material has a molecular weight of 506, and... Figure 6 In the MS spectrum, the maximum molecular weight (median) of compound A is 527. Therefore, 21 of the (26) hydrogens at the substituted positions of the starting material are replaced by deuterium. Thus, it can be calculated that about 81% of the hydrogens are deuterated.

[0222]

[0223] In one exemplary embodiment of this specification, the compound of Formula 1 has one of the following structures.

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232] An exemplary embodiment of this specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound of formula 1.

[0233] The organic material layer of the organic light-emitting device described in this specification can be formed as a single-layer structure, but it can also be formed as a multilayer structure in which two or more organic material layers are stacked. For example, it can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, 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 to this, and it can include a smaller number of organic material layers.

[0234] In one exemplary embodiment of this specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains the aforementioned compound.

[0235] In one exemplary embodiment of this specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains the aforementioned compound as the body of the light-emitting layer.

[0236] In one exemplary embodiment of this specification, the light-emitting layer comprises two or more types of substrates.

[0237] In one exemplary embodiment of this specification, the light-emitting layer comprises two or more mixed substrates, and one or more of the two or more mixed substrates comprises a compound of formula 1.

[0238] In one exemplary embodiment of this specification, the light-emitting layer comprises two or more mixed substrates, one or more of which comprises a compound of Formula 1, and the remainder comprises anthracene compounds. There is no limitation on the anthracene compound, as long as it is an anthracene substrate used in the art.

[0239] In this specification, anthracene compound means a compound containing anthracene moiety.

[0240] In one exemplary embodiment of this specification, the light-emitting layer comprises two bodies.

[0241] In one exemplary embodiment of this specification, the light-emitting layer comprises two substrates, and at least one of the substrates comprises a compound of formula 1.

[0242] In one exemplary embodiment of this specification, the light-emitting layer comprises the above-described compound as a first body, and also comprises a second body of chemical formula H.

[0243] [Chemical formula H]

[0244]

[0245] In the chemical formula H,

[0246] R100 to R109 may be the same or different, and each independently represents hydrogen; deuterium; halogen group; cyano; nitro; hydroxyl; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted heteroaryl; or substituted or unsubstituted silyl.

[0247] In one exemplary embodiment of this specification, R100 to R109 may be the same or different, each being independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0248] In one exemplary embodiment of this specification, R100 to R109 may be the same or different, each being independently hydrogen; deuterium; an aryl group substituted or unsubstituted with one or more of deuterium, aryl and heteroaryl; or a heteroaryl group substituted or unsubstituted with one or more of deuterium, aryl and heteroaryl.

[0249] In one exemplary embodiment of this specification, R100 to R107 may be the same or different, each being independently hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0250] In one exemplary embodiment of this specification, R108 and R109 may be the same or different, each being independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0251] In one exemplary embodiment of this specification, R108 and R109 may be the same or different, each being independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0252] In one exemplary embodiment of this specification, R108 and R109 may be the same or different, each being independently an aryl group substituted or unsubstituted with one or more of deuterium, aryl, and heteroaryl; or a heteroaryl group substituted or unsubstituted with one or more of deuterium, aryl, and heteroaryl.

[0253] In one exemplary embodiment of this specification, the chemical formula H is one of the following structures.

[0254]

[0255]

[0256]

[0257] In one exemplary embodiment of this specification, when the body of the light-emitting layer includes a first body and a second body, the mass ratio of the first body to the second body can 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.

[0258] An organic light-emitting device using two or more hybrid substrates according to an exemplary embodiment of this specification aims to improve device performance by combining the advantages of each substrate. For example, when two substrates are mixed, an organic light-emitting device with high efficiency, low voltage, and long lifetime can be prepared by mixing a substrate with high efficiency and low voltage and a substrate with long lifetime.

[0259] In one exemplary embodiment of this specification, the light-emitting layer has two or more layers, and at least one of the two or more light-emitting layers contains a compound of formula 1.

[0260] In one exemplary embodiment of this specification, the light-emitting layer has two or more layers, at least one of the two or more light-emitting layers contains two or more mixed entities, and at least one of the two or more mixed entities includes a compound of formula 1.

[0261] In one exemplary embodiment of this specification, the organic light-emitting device includes two light-emitting layers (double layer).

[0262] In one exemplary embodiment of this specification, the light-emitting layer is a double layer, and at least one of the two light-emitting layers contains a compound of formula 1.

[0263] In one exemplary embodiment of this specification, the light-emitting layer is a double layer, and one of the two light-emitting layers contains a compound of formula 1.

[0264] In one exemplary embodiment of this specification, the two light-emitting layers are arranged to be in contact with each other.

[0265] In one exemplary embodiment of this specification, the light-emitting layer includes: a first light-emitting layer disposed between a first electrode and a second electrode; and a second light-emitting layer disposed 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 comprises a compound of chemical formula 1.

[0266] In one exemplary embodiment of this specification, the light-emitting layer includes: a first light-emitting layer disposed between a first electrode and a second electrode; and a second light-emitting layer disposed 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 comprises a compound of chemical formula 1, and the other comprises a compound of chemical formula H.

[0267] In one exemplary embodiment of this specification, the first electrode is an anode and the second electrode is a cathode.

[0268] In one exemplary embodiment of this specification, the light-emitting layer includes: a first light-emitting layer disposed between an anode and a cathode; and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein one of the first light-emitting layer and the second light-emitting layer comprises a compound of formula 1.

[0269] In one exemplary embodiment of this specification, the first light-emitting layer comprises a compound of formula 1, and the second light-emitting layer comprises a compound of formula H.

[0270] That is, the light-emitting layer includes: a first light-emitting layer disposed between the anode and the cathode; and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein the first light-emitting layer contains a compound of chemical formula 1, and the second light-emitting layer contains a compound of chemical formula H.

[0271] In one exemplary embodiment of this specification, the first light-emitting layer comprises a compound of chemical formula H, and the second light-emitting layer comprises a compound of chemical formula I.

[0272] That is, the light-emitting layer includes: a first light-emitting layer disposed between the anode and the cathode; and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein the first light-emitting layer contains a compound of chemical formula H, and the second light-emitting layer contains a compound of chemical formula 1.

[0273] In one exemplary embodiment of this specification, the first light-emitting layer comprises a compound of formula 1 as the body of the first light-emitting layer.

[0274] In one exemplary embodiment of this specification, the first light-emitting layer comprises a compound of chemical formula H as the body of the first light-emitting layer.

[0275] In one exemplary embodiment of this specification, the second light-emitting layer comprises a compound of formula 1 as the body of the second light-emitting layer.

[0276] In one exemplary embodiment of this specification, the second light-emitting layer comprises a compound of chemical formula H as the body of the second light-emitting layer.

[0277] In one exemplary embodiment of this specification, at least one of the first light-emitting layer and the second light-emitting layer comprises two or more hybrid substrates. The foregoing description of two or more hybrid substrates is applied herein.

[0278] In one exemplary embodiment of this specification, the first light-emitting layer comprises two or more substrates, and one of the two or more substrates is a compound of formula 1.

[0279] In one exemplary embodiment of this specification, the second light-emitting layer comprises two or more substrates, and one of the two or more substrates is a compound of formula 1.

[0280] In one exemplary embodiment of this specification, the second light-emitting layer comprises two or more substrates, and one of the two or more substrates is a compound of the chemical formula H.

[0281] In one exemplary embodiment of this specification, the first light-emitting layer comprises two substrates, one of which is a compound of formula 1.

[0282] In one exemplary embodiment of this specification, the second light-emitting layer comprises two substrates, one of which is a compound of formula 1.

[0283] In one exemplary embodiment of this specification, the second light-emitting layer comprises two substrates, one of which is a compound of the chemical formula H.

[0284] In one exemplary embodiment of this specification, the maximum emission peak (λ) of the luminescent layer comprising the compound of formula 1 is shown. 最大 The wavelength range is 400 nm to 470 nm.

[0285] In one exemplary embodiment of this specification, the thickness of the light-emitting layer is not limited, but is, for example, from 3 nm to 100 nm. Specifically, it can be from 3 nm to 80 nm, 3 nm to 60 nm, or 3 nm to 30 nm.

[0286] In one exemplary embodiment of this specification, the thicknesses of the first and second light-emitting layers are not limited, as long as the overlap between the first light-emitting layer (single-linear emission region) and the second light-emitting layer (TTF emission region) can be suppressed. For example, the thicknesses of the first and second light-emitting layers are 3 nm to 50 nm, respectively. Specifically, they can be 3 nm to 30 nm, 3 nm to 15 nm, or 3 nm to 10 nm. When the thickness of the light-emitting layer meets the above ranges, it is easy to separate the single-linear emission region and the TTF-derived emission region, and it is easy to suppress the loss of the bulk material of the light-emitting layer.

[0287] In one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant.

[0288] In one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant, and the host comprises a compound represented by chemical formula 1.

[0289] In one exemplary embodiment of this specification, the dopant is a blue dopant.

[0290] In one exemplary embodiment of this specification, the dopant material includes aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives include fused aromatic ring derivatives having substituted or unsubstituted aryl amine groups, such as pyrene, anthracene, etc., having aryl amine groups. Examples of compounds include benzo[a]pyrene, etc. Styrene amine compounds are compounds in which at least one aryl vinyl group is substituted in a substituted or unsubstituted aryl amine. The substituents are selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups, and are either substituted or unsubstituted. Specifically, styrene amine compounds can be styrene amine, styrene diamine, styrene triamine, styrene tetraamine, etc., but are not limited thereto. Metal complexes can include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0291] In one exemplary embodiment of this specification, the dopant includes a fluorescent dopant.

[0292] In one exemplary embodiment of this specification, the fluorescent dopant includes at least one selected from pyrene-based compounds and non-pyrene-based compounds.

[0293] In one exemplary embodiment of this specification, the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound.

[0294] There are no restrictions on pyrene-based and non-pyrene-based compounds, as long as they are compounds used in the art.

[0295] In one exemplary embodiment of this specification, the fluorescent dopant is a non-pyrene-based compound.

[0296] In one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant, the host comprising a compound represented by Formula 1, and the dopant comprising at least one selected from pyrene-based compounds and non-pyrene-based compounds.

[0297] In one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant, the host comprising a compound represented by chemical formula 1, and the dopant comprising a non-pyrene-based compound.

[0298] According to one exemplary embodiment of this specification, non-pyrene-based compounds include at least one of boron-based compounds and diamine-based compounds.

[0299] In one exemplary embodiment of this specification, the boron compound is represented by the chemical formula D or E.

[0300] In one exemplary embodiment of this specification, the diamine compound is represented by the chemical formula F.

[0301] In one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant, the host comprising a compound represented by chemical formula 1, and the dopant comprising one or more compounds of chemical formulas D, E, and F.

[0302] [Chemical formula D]

[0303]

[0304] [Chemical Formula E]

[0305]

[0306] [Chemical formula F]

[0307]

[0308] In chemical formulas D, E, and F,

[0309] Y1 to Y4 may be the same or different, each independently being CR' or NR", and at least one of Y1 and Y2 and at least one of Y3 and Y4 is NR".

[0310] Z1 to Z4 may be the same or different, each being an independently substituted or unsubstituted 5-membered ring; or a substituted or unsubstituted 6-membered ring; or a fused ring of substituted or unsubstituted 5-membered and 6-membered rings.

[0311] R401, R402, R', and R" may be the same or different, 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 amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0312] Lx is a substituted or unsubstituted aryl group; or a substituted or unsubstituted divalent heterocyclic group, provided that Lx is not a divalent pyrene group.

[0313] Ar101 to Ar104 may be the same or different, each being independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0314] r401 and r402 are each integers from 1 to 3, and when r401 and r402 are 2 or greater, the substituents in parentheses are the same or different.

[0315] In one exemplary embodiment of this specification, chemical formula D is one of the following structures.

[0316]

[0317]

[0318]

[0319] In one exemplary embodiment of this specification, chemical formula F is represented by chemical formula F-1.

[0320] [Chemical formula F-1]

[0321]

[0322] In chemical formula F-1,

[0323] Ar101 to Ar104 may be the same or different, each being independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0324] Rd1 and Rd2 may be the same or different, each being independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, and

[0325] rd1 and rd2 are each integers from 1 to 6, and when rd1 and rd2 are 2 or greater, the substituents in parentheses are the same or different.

[0326] In one exemplary embodiment of this specification, Ar101 to Ar104 may be the same or different, each being independently a substituted or unsubstituted aryl group.

[0327] In one exemplary embodiment of this specification, Ar101 to Ar104 may be the same or different, each being independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; or a substituted or unsubstituted naphthyl.

[0328] In one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant, the host comprising the aforementioned compound, and the dopant comprising a compound of chemical formula D or chemical formula E.

[0329] In one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant, the host comprising the aforementioned compound, and the dopant comprising a compound of chemical formula D or chemical formula F.

[0330] In one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant, the host comprising the aforementioned compound, and the dopant comprising a compound of chemical formula D.

[0331] In one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant, the host comprising the aforementioned compound, and the dopant comprising a compound of the chemical formula F.

[0332] In one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant in a weight ratio of 50:50 to 99.9:0.1.

[0333] In one exemplary embodiment of this specification, the organic light-emitting device is a blue organic light-emitting device.

[0334] In one exemplary embodiment of this specification, the organic light-emitting device further includes one or more layers selected from 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.

[0335] In one exemplary embodiment of this specification, the organic light-emitting device includes: a first electrode; a second electrode; a light-emitting layer disposed between the first electrode and the second electrode; and an additional organic material layer disposed between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode.

[0336] In one exemplary embodiment of this specification, the organic light-emitting device includes: a first electrode; a second electrode; a light-emitting layer disposed between the first electrode and the second electrode; and two or more organic material layers disposed between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode.

[0337] In one exemplary embodiment of this specification, the two or more organic material layers between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode may be selected from other light-emitting layers, hole transport layers, hole injection layers, hole injection and transport layers, electron blocking layers, hole blocking layers, electron control layers, hole control layers, electron injection layers, electron transport layers, and electron injection and transport layers.

[0338] In one exemplary embodiment of this specification, two or more organic material layers may be identical organic material layers. For example, the two or more organic material 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.

[0339] In one exemplary embodiment of this specification, the first electrode is an anode or a cathode.

[0340] In one exemplary embodiment of this specification, the second electrode is a cathode or an anode.

[0341] In one exemplary embodiment of this specification, the organic light-emitting device can be an organic light-emitting device (normal type) having a structure in which an anode, one or more layers of organic material, and a cathode are sequentially stacked on a substrate.

[0342] In one exemplary embodiment of this specification, the organic light-emitting device can be an organic light-emitting device (inverted type) having a structure in which a cathode, one or more layers of organic material, and an anode are sequentially stacked on a substrate.

[0343] For example, the structure of an organic light-emitting device according to an exemplary embodiment of this specification is shown in... Figures 1 to 4 middle. Figures 1 to 4 An exemplary organic light-emitting device without limitations is shown.

[0344] Figure 1 The structure of an organic light-emitting device in which a first electrode 2, an organic material layer 10, and a second electrode 3 are stacked in sequence is shown.

[0345] Figure 2 The structure of an organic light-emitting device in which the first electrode 2, the light-emitting layer 4, and the second electrode 3 are sequentially stacked on a substrate 1 is shown.

[0346] Figure 3 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 stacked on a substrate 1 is shown.

[0347] Figure 4The structure of an organic light-emitting device in which the first electrode 2, hole injection layer 5, hole transport layer 6, first light-emitting layer 4-1, second light-emitting layer 4-2, electron control layer 7, electron transport layer 8, electron injection layer 9, and second electrode 3 are sequentially stacked on a substrate 1 is shown.

[0348] Figure 5 The structure of an organic light-emitting device is shown in which the first electrode 2, hole injection layer 5, first hole transport layer 6-1, second hole transport layer 6-2, first light-emitting layer 4-1, second light-emitting layer 4-2, electron control layer 7, electron transport layer 8, electron injection layer 9, and second electrode 3 are sequentially stacked on a substrate 1.

[0349] In one exemplary embodiment of this specification, the light-emitting layer contains the above-described compound.

[0350] The organic light-emitting device described herein can be prepared 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 contain a compound of formula 1.

[0351] When an organic light-emitting device comprises multiple layers of organic materials, the organic material layers can be formed from the same or different materials.

[0352] The organic light-emitting device described in this specification can be fabricated using conventional methods and materials for preparing organic light-emitting devices, except that the light-emitting layer is formed using a compound represented by chemical formula 1.

[0353] For example, the organic light-emitting device of this specification can be fabricated by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. A PVD (physical vapor deposition) method, such as sputtering or electron beam evaporation, can be used to deposit a metal, conductive metal oxide, or alloy thereof on the substrate to form an anode. An organic material layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer can be formed on the anode. Then, a material that can be used as a cathode can be deposited on the organic material layer to fabricate the device. Besides this method, the organic light-emitting device can also be fabricated by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.

[0354] Furthermore, when fabricating organic light-emitting devices, compounds represented by chemical formula 1 can be formed into organic material layers using solution coating and vacuum deposition methods. Solution coating methods include, but are not limited to, spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, and roll coating.

[0355] In addition to these methods, organic light-emitting devices can also be fabricated by sequentially depositing organic material layers from the first electrode material and the second electrode material on a substrate. However, the fabrication methods are not limited to these.

[0356] As the first electrode material, materials with a high work function are generally preferred, which facilitates hole injection into the organic material layer. Examples include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0357] The second electrode material is preferably a material with a low work function to facilitate electron injection into the organic material layer. Examples include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures, such as LiF / Al or LiO2 / Al, but not limited thereto.

[0358] The light-emitting layer may comprise a host material and a dopant material. When the organic light-emitting device includes an additional light-emitting layer besides one comprising a compound of Formula 1 according to an exemplary embodiment of this specification, the host material may be a fused and / or non-fused aromatic ring derivative, a heterocyclic compound, etc. Specifically, fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc. The dopant material is the same as described above.

[0359] The hole injection layer is a layer that receives holes from the electrode. Specifically, materials with the ability to transport holes and exhibiting excellent effects in receiving holes from the anode and in hole injection into the light-emitting layer or light-emitting material can be used as hole injection materials. Furthermore, materials with excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection material are desirable. Additionally, materials with excellent thin film forming capabilities are desirable. Furthermore, it is desirable that the HOMO (highest occupied molecular orbital) of the hole injection material lies between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of hole injection materials include metalloporphyrins, oligothiophenes, arylamine compounds, quinoxaline-based compounds, hexanitrile hexaazabenzophenanthrene-based compounds, quinacridone-based compounds, and others. Compounds, benzyl nitrile-based compounds, anthraquinones, and conductive polymers of polyaniline and polythiophene, but not limited thereto.

[0360] In one exemplary embodiment of this specification, the hole injection layer comprises a compound with the chemical formula HI-A.

[0361] [Chemical formula HI-A]

[0362]

[0363] In the chemical formula HI-A,

[0364] R h1 To R h6 The same or different, each independently being hydrogen; deuterium; cyano; substituted or unsubstituted amino; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0365] In one exemplary embodiment of this specification, R h1 To R h6 Each is a cyano group.

[0366] In one exemplary embodiment of this specification, the chemical formula HI-A has the following structure.

[0367]

[0368] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. Materials with high hole mobility that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer are preferred as hole transport materials. 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.

[0369] In one exemplary embodiment of this specification, the hole transport layer comprises one or more compounds of the chemical formulas HT-1 and HT-2.

[0370] [Chemical formula HT-1]

[0371]

[0372] [Chemical formula HT-2]

[0373]

[0374] In chemical formulas HT-1 and HT-2,

[0375] Rs1 to Rs5 may be the same or different, each being independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0376] Ls1 and Ls2 may be the same or different, each being a direct bond independently; or they may be substituted or unsubstituted aryl groups.

[0377] Ars1 to Ars4 may be the same or different, each being independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0378] rs2, rs4, and rs5 are each integers from 1 to 4, and rs3 is an integer from 1 to 3. When rs2 to rs5 are each 2 or greater, the substituents in parentheses are the same or different.

[0379] In one exemplary embodiment of this specification, Rs1 to Rs5 may be the same or different, each being independently hydrogen or deuterium.

[0380] In one exemplary embodiment of this specification, Ls1 and Ls2 may be the same or different, each being independently a substituted or unsubstituted aryl group.

[0381] In one exemplary embodiment of this specification, Ls1 and Ls2 may be the same or different, each being independently a substituted or unsubstituted phenylene; or a substituted or unsubstituted biphenylene.

[0382] In one exemplary embodiment of this specification, Ars1 to Ars4 may be the same or different, each being independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; or a substituted or unsubstituted naphthyl.

[0383] In one exemplary embodiment of this specification, the chemical formula HT-1 has the following structure.

[0384]

[0385] In one exemplary embodiment of this specification, the chemical formula HT-2 has the following structure.

[0386]

[0387] In one exemplary embodiment of this specification, the hole transport layer may be composed of a first hole transport layer and a second hole transport layer.

[0388] In one exemplary embodiment of this specification, the first hole transport layer may comprise a compound of the chemical formula HT-1.

[0389] In one exemplary embodiment of this specification, the second hole transport layer may comprise a compound with the chemical formula HT-2.

[0390] A hole control layer is a layer that improves device lifetime and efficiency by controlling holes transported from a hole transport layer, allowing them to be smoothly injected into the light-emitting layer and preventing electrons injected from an electron injection layer from passing through the light-emitting layer into the hole injection layer. Any known material can be used without restriction, and the hole control layer 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.

[0391] The electron control layer is a layer that controls the smooth injection of electrons from the electron transport layer into the light-emitting layer, and any known material can be used without restriction.

[0392] In one exemplary embodiment of this specification, the electronic control layer includes replaced or unreplaced components. Ton-based; or substituted or unsubstituted spirofluorene-9,9'- Ton base.

[0393] In one exemplary embodiment of this specification, the electronic control layer comprises a compound with the chemical formula EB-A.

[0394] [Chemical Formula EB-A]

[0395]

[0396] In the chemical formula EB-A,

[0397] Rb1 and Rb2 may be the same or different, each being independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, and

[0398] rb1 and rb2 are each integers from 1 to 8, and when rb1 and rb2 are 2 or greater, the substituents in parentheses are the same or different.

[0399] In one exemplary embodiment of this specification, Rb1 and Rb may be the same or different, each being independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0400] In one exemplary embodiment of this specification, Rb1 is hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0401] In one exemplary embodiment of this specification, Rb1 is hydrogen; deuterium; substituted or unsubstituted phenyl; or substituted or unsubstituted biphenyl.

[0402] In one exemplary embodiment of this specification, Rb1 is hydrogen; deuterium; or a substituted heteroaryl-substituted phenyl group.

[0403] In one exemplary embodiment of this specification, Rb1 is hydrogen; deuterium; or an aryl-substituted phenyl group.

[0404] In one exemplary embodiment of this specification, Rb1 is hydrogen; deuterium; or a triazine-substituted phenyl group substituted with an aryl group.

[0405] In one exemplary embodiment of this specification, Rb2 is hydrogen; or deuterium.

[0406] In one exemplary embodiment of this specification, the chemical formula EB-A has the following structure.

[0407]

[0408] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As an electron transport material, a material with high electron mobility that can effectively receive electrons from the cathode and transport them to the light-emitting layer is desirable. Examples of electron transport materials include, but are not limited to, those selected from fluorenone, anthraquinone dimethylane, biphenylquinone, thiam dioxide, etc. azole, diazole, triazole, triazine, imidazole Organic compounds of tetracarboxylic acids, fluorenemethane and anthrone, and their derivatives; metal complexes; and nitrogen-containing 5-membered ring derivatives; etc.

[0409] Metal complex compounds include lithium quinoline (Liq), bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but are not limited to these.

[0410] In one exemplary embodiment of this specification, the electron transport layer may simultaneously comprise organic compounds and metal complexes.

[0411] In one exemplary embodiment of this specification, the electron transport layer comprises a compound represented by the chemical formula ET-A.

[0412] [Chemical formula ET-A]

[0413]

[0414] In the chemical formula ET-A,

[0415] At least one of Z11 to Z13 is N, and the rest are CH.

[0416] At least one of Z21 to Z23 is N, and the rest are CH.

[0417] L601 and L602 may be the same or different, each being a direct bond; substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups, and

[0418] Ar601 to Ar604 may be the same or different, each being independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0419] In one exemplary embodiment of this specification, L601 and L602 may be the same or different, each being independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0420] In one exemplary embodiment of this specification, L601 and L602 may be the same or different, each being independently aryl.

[0421] In one exemplary embodiment of this specification, L601 and L602 are phenylene oxides.

[0422] In one exemplary embodiment of this specification, Ar601 to Ar604 may be the same or different, each being independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0423] In one exemplary embodiment of this specification, Ar601 to Ar604 may be the same or different, each being independently aryl.

[0424] In one exemplary embodiment of this specification, Ar601 to Ar604 are substituted or unsubstituted phenyl groups.

[0425] In one exemplary embodiment of this specification, Ar601 to Ar604 are cyano-substituted or unsubstituted phenyl groups.

[0426] In one exemplary embodiment of this specification, the compound of chemical formula ET-A is any of the following compounds.

[0427]

[0428] The electron injection layer is a layer that receives electrons from the electrode. As an electron injection material, it is desirable to have excellent electron transport capabilities and exhibit both the effect of receiving electrons from the second electrode and the effect of injecting electrons into the light-emitting layer or light-emitting material. Furthermore, it is desirable to have materials that prevent excitons generated in the light-emitting layer from migrating to the hole injection layer and possess excellent thin film formation capabilities. Specifically, these can be fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, diazole, triazole, imidazole, Tetracarboxylic acids, fluorenemethane, anthrone, and their derivatives, metal complex compounds, nitrogen-containing five-membered ring derivatives, etc., but not limited to these.

[0429] Metal complex compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but are not limited to these.

[0430] An electron blocking layer is a layer that improves device lifetime and efficiency by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. Any known material can be used without restriction, and the electron blocking layer 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.

[0431] A hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed under the same conditions as the electron injection layer. Specifically, it can be used... Diazole derivatives, triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, etc., but not limited to these.

[0432] A capping layer is formed to prevent a significant amount of light loss in organic light-emitting devices due to total internal reflection. The capping layer effectively protects the underlying cathode and light-emitting layer from external moisture penetration or contamination, and prevents light loss through total internal reflection due to its high refractive index. Conventional materials can be used without restriction.

[0433] Depending on the materials used, the organic light-emitting device according to this specification can be a front-emitting, rear-emitting, or dual-sided emitting type.

[0434] The organic light-emitting devices according to this specification can be included in and used in various electronic devices. For example, electronic devices can be display panels, touch panels, solar modules, lighting devices, etc., but are not limited thereto.

[0435] Invention Embodiments

[0436] This specification will be specifically described below through examples, comparative examples, etc. However, the examples and comparative examples described in this specification can be modified in various different ways, and the scope of this specification is not to be construed as limited to the examples and comparative examples. The examples and comparative examples in this specification are provided to illustrate this specification more completely to those skilled in the art.

[0437] <Preparation Example>

[0438] Preparation Example 1. Synthesis of Intermediate A

[0439]

[0440] Preparation Example 1-1) Synthesis of Intermediate A-1

[0441] SM1 (1 equivalent) and SM2 (1.1 equivalent) were added to tetrahydrofuran (THF, 10 times that of SM1). Then, after adding 2 M aqueous potassium carbonate solution (30 vol% of THF) and tetra-triphenyl-phosphine palladium (2 mol%), the mixture was heated with stirring for 10 hours. After lowering the temperature to room temperature and allowing the reaction to complete, the aqueous potassium carbonate solution was removed by chromatography, and then THF was removed by distillation under reduced pressure. After dissolving in chloroform and placing in a separatory funnel, the mixture was washed three times with distilled water, and the organic material layer was dried over anhydrous magnesium sulfate. The chloroform was then removed under reduced pressure, and intermediate A-1 was obtained as a solid by recrystallization in hexane.

[0442] Preparation Example 1-2) Synthesis of Intermediate A

[0443] Intermediate A-1 (1 equivalent) and bis(pinacol)diboron (1.5 equivalent) were added to 1,4-di After adding alkylene (12 times the amount of intermediate A-1), potassium acetate (3.0 equivalents) was added and the mixture was refluxed with stirring. Palladium acetate (0.02 equivalents) and tricyclohexylphosphine (0.04 equivalents) were then added to 1,4-dialkylene oxide. In alkanes, the mixture was stirred for 5 minutes, and the reaction was confirmed to be complete after 2 hours. The mixture was then cooled to room temperature. The 1,4-dioxane was removed by distillation under reduced pressure. After adding the alkyl group, ethanol and water were added. After filtration, intermediate A was prepared by recrystallization with ethyl acetate and ethanol.

[0444] Preparation Example 2. Synthesis of Intermediate B

[0445]

[0446] Preparation Example 2-1) Synthesis of Intermediate B-1

[0447] Intermediate B-1 was obtained in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the reaction scheme above.

[0448] Preparation Example 2-2) Synthesis of Intermediate B

[0449] Intermediate B was prepared in the same manner as in Preparation Examples 1-2, except that intermediate B-1 was used instead of intermediate A-1.

[0450] Preparation Example 3. Synthesis of Intermediate C

[0451]

[0452] Preparation Example 3-1) Synthesis of Intermediate C-1

[0453] Intermediate C-1 was obtained in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the above reaction scheme.

[0454] Preparation Example 3-2) Synthesis of Intermediate C

[0455] Intermediate C was prepared in the same manner as in Preparation Examples 1-2, except that intermediate C-1 was used instead of intermediate A-1.

[0456] Preparation Example 4. Synthesis of Intermediate D

[0457]

[0458] Preparation Example 4-1) Synthesis of Intermediate D-1

[0459] Through documents such as literature<ACS Appl. Mater. Interfaces 2017, 9, 15, 13785> The synthesis described herein yields intermediate D-1.

[0460] Preparation Example 4-2) Synthesis of Intermediate D

[0461] Intermediate D was prepared in the same manner as in Preparation Examples 1-2, except that intermediate D-1 was used instead of intermediate A-1.

[0462] Preparation Example 5. Synthesis of Intermediate E

[0463]

[0464] Preparation Example 5-1) Synthesis of Intermediate E-1

[0465] Intermediate E-1 was obtained in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the above reaction scheme.

[0466] Preparation Example 5-2) Synthesis of Intermediate E

[0467] Intermediate E was prepared in the same manner as in Preparation Examples 1-2, except that intermediate E-1 was used instead of intermediate A-1.

[0468] Preparation Example 6. Synthesis of Intermediate F

[0469]

[0470] Preparation Example 6-1) Synthesis of Intermediate F-1

[0471] Intermediate F-1 was obtained in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the above reaction scheme.

[0472] Preparation Example 6-2) Synthesis of Intermediate F

[0473] Intermediate F was prepared in the same manner as in Preparation Examples 1-2, except that intermediate F-1 was used instead of intermediate A-1.

[0474] Preparation Example 7. Synthesis of Compound BH-1

[0475]

[0476] Preparation Example 7-1) Synthesis of compound BH-1-1

[0477] Compound BH-1-1 was obtained in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the above reaction scheme.

[0478] Preparation Example 7-2) Synthesis of Compound BH-1

[0479] Compound BH-1-1 and AlCl3 (20 wt%) were added to C6D6 (20 times the amount of BH-1-1) and stirred for 2 hours. After the reaction was complete, D2O (1.5 times the amount of compound BH-1-1) was added. After stirring for 30 minutes, trimethylamine (1 / 10 the amount of D2O) was added. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4 and recrystallized in ethyl acetate to prepare compound BH-1.

[0480] Preparation Example 8. Synthesis of Compound BH-2

[0481]

[0482] Preparation Example 8-2) Synthesis of compound BH-2

[0483] Compound BH-2 was prepared in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the above reaction scheme.

[0484] Preparation Example 9. Synthesis of Compound BH-3

[0485]

[0486] Compound BH-3 was prepared in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the above reaction scheme.

[0487] Preparation Example 10. Synthesis of Compound BH-4

[0488]

[0489] Preparation Example 10-1) Synthesis of compound BH-4-1

[0490] Compound BH-4-1 was obtained in the same manner as in Preparation Example 1-1, except that 1-bromo-3-chlorobenzene and intermediate F were used instead of SM1 and SM2.

[0491] Preparation Example 10-2) Synthesis of compound BH-4-2

[0492] Compound BH-4-2 was obtained in the same manner as in Preparation Examples 1-2, except that compound BH-4-1 was used instead of intermediate A-1.

[0493] Preparation Example 10-3) Synthesis of compound BH-4-3

[0494] Compound BH-4-3 was obtained in the same manner as in Preparation Example 1-1, except that 1-bromopyrene and compound BH-4-2 were used instead of SM1 and SM2.

[0495] Preparation Example 10-4) Synthesis of compound BH-4

[0496] Compound BH-4 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-4-3 was used instead of compound BH-1-1.

[0497] Preparation Example 11. Synthesis of Compound BH-5

[0498]

[0499] Preparation Example 11-1) Synthesis of compound BH-5-1

[0500] Compound BH-5-1 was obtained in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the reaction scheme above.

[0501] Preparation Example 11-2) Synthesis of compound BH-5

[0502] Compound BH-5 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-5-1 was used instead of compound BH-1-1.

[0503] Preparation Example 12. Synthesis of Compound BH-6

[0504]

[0505] Preparation Example 12-1) Synthesis of compound BH-6-1

[0506] Compound BH-6-1 was obtained in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the reaction scheme above.

[0507] Preparation Example 12-2) Synthesis of compound BH-6-2

[0508] Compound BH-6-1 (1 equivalent) was dissolved in acetonitrile (AN, 20 times the amount of compound BH-6-1), and then an aqueous solution of potassium carbonate (2.5 equivalents) (30% by weight) was added. Then, 1.5 equivalents of nonafluorobutane-1-sulfonyl fluoride was slowly added dropwise while stirring (at room temperature). The reaction was confirmed to be complete after 5 hours. After removing the acetonitrile by distillation under reduced pressure, the product was dissolved in chloroform and extracted several times with water. The organic material layer was dried over anhydrous magnesium sulfate. Compound BH-6-2 was prepared by purification via recrystallization using ethanol after removing the organic solvent by distillation under reduced pressure.

[0509] Synthesis of compound BH-6-3 (Preparation Example 12-3)

[0510] Compound BH-6-3 was obtained in the same manner as in Preparation Examples 1-2, except that compound BH-6-2 was used instead of intermediate A-1.

[0511] Synthesis of compound BH-6-4 (Preparation Example 12-4)

[0512] Compound BH-6-4 was obtained in the same manner as in Preparation Example 1-1, except that 7-chloronaphthofuran and compound BH-6-3 were used instead of SM1 and SM2.

[0513] Synthesis of compound BH-6 (Preparation Example 12-5)

[0514] Compound BH-6 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-6-4 was used instead of compound BH-1-1.

[0515] Preparation Example 13. Synthesis of Compound BH-7

[0516]

[0517] Preparation Example 13-1) Synthesis of Compound BH-7-1

[0518] SM1 (1,8-dibromopyrene, 1 equivalent) and SM2 (intermediate E, 2.2 equivalents) were added to tetrahydrofuran (THF, 10 times that of 1,8-dibromopyrene). Then, after adding 2 M aqueous potassium carbonate solution (30 vol% of THF) and tetra-triphenyl-phosphine palladium (2 mol%), the mixture was heated with stirring for 10 hours. After lowering the temperature to room temperature and allowing the reaction to complete, the aqueous potassium carbonate solution was removed by chromatography, and then THF was removed by distillation under reduced pressure. After dissolving in chloroform and placing in a separatory funnel, the organic material layer was washed three times with distilled water and dried over anhydrous magnesium sulfate. Then, after removing the chloroform under reduced pressure, the compound BH-7-1 was obtained as a solid by recrystallization with EA (ethyl acetate).

[0519] Preparation Example 13-2) Synthesis of Compound BH-7

[0520] Compound BH-7 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-7-1 was used instead of compound BH-1-1.

[0521] Preparation Example 14. Synthesis of Compound BH-8

[0522]

[0523] Preparation Example 14-1) Synthesis of Compound BH-8-1

[0524] Compound BH-8-1 was obtained in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the above reaction scheme.

[0525] Preparation Example 14-2) Synthesis of compound BH-8-2

[0526] Compound BH-8-2 was obtained in the same manner as in Preparation Example 12-2, except that compound BH-8-1 was used instead of compound BH-6-1.

[0527] Preparation Example 14-3) Synthesis of compound BH-8-3

[0528] Compound BH-8-3 was obtained in the same manner as in Preparation Example 12-3, except that compound BH-8-2 was used instead of compound BH-6-2.

[0529] Preparation Example 14-4) Synthesis of compound BH-8-4

[0530] Compound BH-8-4 was obtained in the same manner as in Preparation Example 1-1, except that intermediate F and compound BH-8-3 were used instead of SM1 and SM2.

[0531] Synthesis of compound BH-8 (Preparation Example 14-5)

[0532] Compound BH-8 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-8-4 was used instead of compound BH-1-1.

[0533] Preparation Example 15. Synthesis of Compound BH-9

[0534]

[0535] Preparation Example 15-1) Synthesis of Compound BH-9-1

[0536] Compound BH-9-1 was obtained in the same manner as in Preparation Examples 1-2, except that 5-chloronaphtho[1,2-b]furan was used instead of intermediate A-1.

[0537] Preparation Example 15-2) Synthesis of compound BH-9-2

[0538] Compound BH-9-2 was obtained in the same manner as in Preparation Example 13-1, except that 1,6-dibromopyrene and compound BH-9-1 were used instead of 1,8-dibromopyrene and intermediate E.

[0539] Preparation Example 15-3) Synthesis of Compound BH-9

[0540] Compound BH-9 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-9-2 was used instead of compound BH-1-1.

[0541] Preparation Example 16. Synthesis of Compound BH-10

[0542]

[0543] Preparation Example 16-1) Synthesis of compound BH-10-1

[0544] Compound BH-10-1 was obtained in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the reaction scheme above.

[0545] Preparation Example 16-2) Synthesis of compound BH-10-2

[0546] Compound BH-10-1 (1 equivalent) and intermediate B (1.1 equivalent) were added to 1,4-di In alkyl (10 times that of compound BH-10-1). Then, add 2 M potassium phosphate aqueous solution (1,4-dialkyl ... After adding 30 vol% (30 vol%) of alkylene and bis(tri-tert-butylphosphine)palladium (0) (1 mol%), the mixture was heated for 10 hours with stirring. After lowering the temperature to room temperature and completing the reaction, the aqueous potassium phosphate solution was removed by chromatography. Then, 1,4-di(2 ... Alkane. After being dissolved in chloroform and placed in a separatory funnel, the mixture was washed three times with distilled water, and the organic material layer was dried over anhydrous magnesium sulfate. The compound BH-10-2 was obtained as a solid by removing the chloroform under reduced pressure and recrystallizing from EA (ethyl acetate).

[0547] Preparation Example 16-3) Synthesis of Compound BH-10

[0548] Compound BH-10 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-10-2 was used instead of compound BH-1-1.

[0549] Preparation Example 17. Synthesis of Compound BH-11

[0550]

[0551] Preparation Example 17-1) Synthesis of compound BH-11-1

[0552] Compound BH-11-1 was obtained in the same manner as in Preparation Example 1-1, except that SM1 and SM2 were changed as in the reaction scheme above.

[0553] Preparation Example 17-2) Synthesis of compound BH-11-2

[0554] Compound BH-11-2 was obtained in the same manner as in Preparation Example 16-2, except that compound BH-10-1 and intermediate B were used instead of compound BH-11-1 and intermediate D.

[0555] Synthesis of compound BH-11 (Preparation Example 17-3)

[0556] Compound BH-11 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-11-2 was used instead of compound BH-1-1.

[0557] Preparation Example 18. Synthesis of Compound BH-12

[0558]

[0559] Preparation Example 18-1) Synthesis of compound BH-12-1

[0560] Compound BH-12-1 was obtained in the same manner as in Preparation Example 13-1, except that 4,10-dibromopyrene and intermediate B were used instead of 1,8-dibromopyrene and intermediate E.

[0561] Preparation Example 18-2) Synthesis of Compound BH-12

[0562] Compound BH-12 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-12-1 was used instead of compound BH-1-1.

[0563] Preparation Example 19. Synthesis of Compound BH-13

[0564]

[0565] Preparation Example 19-1) Synthesis of compound BH-13-1

[0566] Compound BH-13-1 was obtained in the same manner as in Preparation Examples 1-2, except that 4-chloronaphtho[2,3-b]furan was used instead of intermediate A-1.

[0567] Preparation Example 19-2) Synthesis of compound BH-13-2

[0568] Compound BH-13-2 was obtained in the same manner as in Preparation Example 1-1, except that compounds BH-13-1 and 1-bromo-2-chlorobenzene were used instead of SM1 and SM2.

[0569] Synthesis of compound BH-13-3 (Preparation Example 19-3)

[0570] Compound BH-13-3 was obtained by synthesizing compound BH-13-3 in the same manner as in Preparation Examples 1-2, except that compound BH-13-2 was used instead of intermediate A-1.

[0571] Synthesis of compound BH-13-4 (Preparation Example 19-4)

[0572] Compound BH-13-4 was obtained in the same manner as in Preparation Example 13-1, except that 2,7-dibromopyrene and compound BH-13-3 were used instead of 1,8-dibromopyrene and intermediate E.

[0573] Synthesis of compound BH-13 (Preparation Example 19-5)

[0574] Compound BH-13 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-13-4 was used instead of compound BH-1-1.

[0575] Preparation Example 20. Synthesis of Compound BH-14

[0576]

[0577] Preparation Example 20-1) Synthesis of compound BH-14-1

[0578] Compound BH-14-1 was obtained by synthesizing compound BH-14-1 in the same manner as in Preparation Example 1-1, except that 1-bromo-6-chloropyrene and intermediate E were used instead of SM1 and SM2.

[0579] Preparation Example 20-2) Synthesis of compound BH-14-2

[0580] Compound BH-14-2 was obtained in the same manner as in Preparation Example 16-2, except that compound BH-14-1 was used instead of compound BH-10-1.

[0581] Preparation Example 20-3) Synthesis of compound BH-14

[0582] Compound BH-14 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-14-2 was used instead of compound BH-1-1.

[0583] Preparation Example 21. Synthesis of Compound BH-15

[0584]

[0585] Preparation Example 21-1) Synthesis of compound BH-15-1

[0586] Compound BH-15-1 was obtained in the same manner as in Preparation Example 1-1, except that SM1-1 and intermediate F were used instead of SM1 and SM2.

[0587] Synthesis of compound BH-15-2 (Preparation Example 21-2)

[0588] Compound BH-15-2 was obtained in the same manner as in Preparation Example 13-1, except that compound BH-15-1 and phenylboronic acid were used instead of 1,8-dibromopyrene and intermediate E.

[0589] Synthesis of compound BH-15 (Preparation Example 21-3)

[0590] Compound BH-15 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-15-2 was used instead of compound BH-1-1.

[0591] Preparation Example 22. Synthesis of Compound BH-16

[0592]

[0593] Preparation Example 22-1) Synthesis of compound BH-16-1

[0594] Compound BH-16-1 was obtained in the same manner as in Preparation Example 13-1, except that SM1 and SM2 were changed as in the above reaction scheme.

[0595] Preparation Example 22-2) Synthesis of compound BH-16-2

[0596] Compound BH-16-1 (1 equivalent) and phenylboronic acid (2.2 equivalents) were added to 1,4-diphenylboronic acid. Alkane (1,4-di) Alkane, compound BH-16-1 (10 times). Then, 2 M potassium phosphate aqueous solution (1,4-dialkylene) was added. After adding 30 vol% (30 vol%) of alkylene and bis(tri-tert-butylphosphine)palladium (0) (1 mol%), the mixture was heated for 10 hours with stirring. After the temperature was lowered to room temperature and the reaction was completed, the aqueous potassium phosphate solution was removed by chromatography, and then 1,4-di(2 ... Alkane. After being dissolved in chloroform and placed in a separatory funnel, the mixture was washed three times with distilled water, and the organic material layer was dried over anhydrous magnesium sulfate. The chloroform was then removed under reduced pressure, and the compound BH-16-2 was obtained as a solid by recrystallization from ethyl acetate (EA).

[0597] Synthesis of compound BH-16 (Preparation Example 22-3)

[0598] Compound BH-16 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-16-2 was used instead of compound BH-1-1.

[0599] Preparation Example 23. Synthesis of Compound BH-17

[0600]

[0601] Preparation Example 23-1) Synthesis of compound BH-17-1

[0602] 1,3,6,8-Tetrabromopyrene (1 equivalent) and intermediate C (4.4 equivalents) were added to tetrahydrofuran (THF, 20 times that of 1,3,6,8-tetrabromopyrene). Then, after adding 8 M aqueous potassium carbonate solution (30 vol% of THF) and tetratriphenyl-phosphine palladium (8 mol%), the mixture was heated with stirring for 10 hours. After lowering the temperature to room temperature and allowing the reaction to complete, the aqueous potassium carbonate solution was removed by chromatography, and then THF was removed by distillation under reduced pressure. After dissolving in chloroform and placing in a separatory funnel, the organic material layer was washed three times with distilled water and dried over anhydrous magnesium sulfate. The chloroform was then removed under reduced pressure, and the compound BH-17-1 was obtained as a solid by recrystallization in toluene.

[0603] Preparation Example 23-2) Synthesis of Compound BH-17

[0604] Compound BH-17 was prepared in the same manner as in Preparation Example 7-2, except that compound BH-17-1 was used instead of compound BH-1-1.

[0605] <Example>

[0606] Example 1.

[0607] On it, ITO (indium tin oxide) / Ag / ITO is deposited to 70. / 1000 / 70 The substrate, used as the anode, was cut into 50 mm × 50 mm × 0.5 mm pieces, placed in distilled water containing a dispersant, and ultrasonically washed. The detergent was a product of Fischer Co., and the distilled water was filtered twice using a Millipore Co. filter. The ITO was washed for 30 minutes, then ultrasonically washed twice with distilled water for 10 minutes each time. After washing with distilled water, the ITO was ultrasonically washed sequentially with isopropanol, acetone, and methanol, and then dried.

[0608] A hole injection layer was formed on the prepared transparent ITO electrode by thermal vacuum deposition of the HAT-CN compound to a thickness of 5 nm. Next, 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. Next, compounds BH-2 (body 1) and BD-1 (dopant) synthesized in the preparation example were simultaneously vacuum deposited (body 1 compound:dopant compound weight ratio = 95:5) to form a hole transport layer with a thickness of 85 nm. The first luminescent layer is formed. Next, compound BH-A (body 2) and compound BD-1 (doper) are simultaneously vacuum-deposited (body 2 compound:doper compound weight ratio = 95:5) to form a layer with a thickness of 85 mm. The second light-emitting layer is then deposited. Next, ETL2 is deposited to form a thickness of 50 μm. The electronic control layer was constructed by mixing compound ETL1 and lithium quinoline (Liq) in a 7:3 ratio to form a thickness of 250 mm. Electron transport layer. Magnesium and lithium fluoride (LiF) were sequentially deposited as electron injection layers to a depth of 50 μm. The thickness.

[0609] Using magnesium and silver (1:4) to form a thickness of 200 After the cathode, CP1 was deposited to 600 The thickness is used to complete the device. The deposition rate of organic material is maintained at 1. / Second.

[0610]

[0611]

[0612] Examples 2 to 32 and Comparative Examples 1 to 3.

[0613] Organic light-emitting devices were prepared 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.

[0614] In the subjects described in Table 1, the compounds represented by chemical formula 1 (compounds BH-2 to BH-17) of this disclosure were prepared in the same manner as in preparation examples 8 to 23.

[0615] The BH-C, BH-K, and BH-L used in Comparative Examples 1 to 3 are as follows.

[0616]

[0617] For the organic light-emitting devices prepared in Examples 1 to 32 and Comparative Examples 1 to 10, at 10 mA / cm 2 Measure the driving voltage (V) at current density oc ) and luminous efficacy (cd / A), and at 20 mA / cm 2 The time (LT) to reach 95% of the initial brightness was measured at a given current density. The results are shown in Table 1.

[0618] [Table 1]

[0619]

[0620] As shown in Table 1, organic light-emitting devices using compounds of the present disclosure in the light-emitting layer exhibit excellent lifetime characteristics.

[0621] On the other hand, organic light-emitting devices that use compounds other than those of Formula 1 in the light-emitting layer exhibit reduced lifetime characteristics.

Claims

1. A compound of Chemical Formula 1: [Chemical Formula 1] in Chemical Formula 1, one to four of R2 to R5 and R7 to R10 are bonded to Chemical Formula 2, the rest of R2 to R5 and R7 to R10 are the same or different, each independently hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, and R1 and R6 are the same or different, each independently hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, [Chemical Formula 2] in Chemical Formula 2, X is O or S, A1, A2, and R11 are the same or different, each independently hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, L1 is a direct bond; substituted or unsubstituted arylene; or substituted or unsubstituted heteroarylene, l1 is an integer of 1 to 4, and if l1 is 2 or more, two or more L1 are the same or different, r11 is an integer of 1 to 5, and if r11 is 2 or more, two or more R11 are the same or different.

2. The compound according to claim 1, wherein Chemical Formula 2 is any one of Chemical Formula 2-1 to Chemical Formula 2-3: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] in Chemical Formula 2-1 to Chemical Formula 2-3, X is O or S, L1 is a direct bond; substituted or unsubstituted arylene; or substituted or unsubstituted heteroarylene, A1, A2, R12, and R13 are the same or different, each independently hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, l1 is an integer of 1 to 4, and if l1 is 2 or more, two or more L1 are the same or different, r12 is 1 or 2, r13 is an integer of 1 to 4, r12 + r13 is an integer of 1 to 5, and when r12 and r13 are 2 or more, the substituents in the parentheses are the same or different.

3. The compound according to claim 1, wherein Chemical Formula 1 is Chemical Formula 1-1 or Chemical Formula 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] in Chemical Formula 1-1 and Chemical Formula 1-2, R1 to R10 are the same or different, each independently hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, and 4. The compound according to claim 1, wherein Chemical Formula 1 is any one of Chemical Formula 1-11 to Chemical Formula 1-20: [Chemical Formula 1-11] [Chemical Formula 1-12] [Chemical Formula 1-13] [Chemical Formula 1-14] [Chemical Formula 1-15] [Chemical Formula 1-16] [Chemical Formula 1-17] [Chemical Formula 1-18] [Chemical Formula 1-19] [Chemical Formula 1-20] in Chemical Formula 1-11 to Chemical Formula 1-20, ​ ​ ​ ​ ​ ​ ​ ​ ​ is a moiety bonded to Formula 1. ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ is a moiety bonded to Formula 1. ​ ​ ​ is a moiety for bonding to Chemical Formula 2. ​ ​ R1to R10are the same or different, each independently hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, and is a moiety for bonding to Chemical Formula 2.

5. The compound of claim 1, wherein Chemical Formula 1 is any one of Chemical Formula 1-31 to Chemical Formula 1-35: In Chemical Formula 1-31 to Chemical Formula 1-35, R1and R3to R10are the same or different, each independently hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, and is a moiety for bonding to Chemical Formula 2.

6. The compound of claim 1, wherein one to four of R2to R5and R7to R10are bonded to Chemical Formula 2, and the rest of R2to R5and R7to R10are the same or different, each independently hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted benzophenanthryl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiophenyl.

7. The compound of claim 1, wherein R1and R6are the same or different, each independently hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiophenyl.

8. The compound of claim 1, wherein A1and A2are the same or different, each independently hydrogen; deuterium; or substituted or unsubstituted aryl.

9. The compound of claim 1, wherein the compound is a compound having any one of the following structures: 。 10. An organic light emitting device comprising: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the compound of any one of claims 1 to 9.

11. The organic light-emitting device of claim 10, wherein the organic material layers include an emission layer, and the emission layer comprises the compound.

12. The organic light-emitting device of claim 10, wherein the organic material layers include an emission layer, and the emission layer comprises the compound.

13. The organic light-emitting device of claim 11, wherein the emission layer comprises a host and a dopant, the host comprises the compound, the dopant comprises one or more compounds selected from the group consisting of Chemical Formula D, Chemical Formula E, and Chemical Formula F: [Chemical Formula D] [Chemical Formula E] [Chemical Formula F] In Chemical Formula D, Chemical Formula E, and Chemical Formula F, Y1to Y4are the same or different, each independently CR' or NR", at least one of Y1and Y2and at least one of Y3and Y4are NR", Z1to Z4are the same or different, each independently a substituted or unsubstituted 5-membered ring; a substituted or unsubstituted 6-membered ring; or a fused ring of a substituted or unsubstituted 5-membered ring and a 6-membered ring, R401, R402, R' and R" are the same or different, each independently 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 bonded to an adjacent group to form a substituted or unsubstituted ring, Lx is a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group, with the proviso that Lx is not a divalent pyrene group, Ar101to Ar104are the same or different, each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and r401and r402are each an integer of 1 to 3, and when r401and r402are 2 or more, the substituents in the parentheses are the same or different.

14. The organic light emitting device according to claim 11, wherein the light emitting layer comprises the compound as a first host, and further comprises a compound of Chemical Formula H as a second host: [Chemical Formula H] in Chemical Formula H, R100to R109are the same or different, each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl 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. The organic light emitting device of claim 11, wherein the light emitting layer comprises: a first light emitting layer disposed between the first electrode and the second electrode; and a second light emitting layer disposed between the first light emitting layer and the second electrode and in contact with the first light emitting layer, and one of the first light emitting layer and the second light emitting layer comprises the compound.

16. The 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 Chemical Formula H: [Chemical Formula H] in Chemical Formula H, R100to R109are the same or different, each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl 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. The organic light emitting device according to claim 15, wherein the first light emitting layer comprises two or more hosts, and any one of the two or more hosts is the compound.

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