Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device comprising the same.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2023-0135702 filed with the Korean Patent Office on October 12, 2023, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a compound and an organic light-emitting device including the same. Background Art

[0003] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting generally has a structure including an anode and a cathode and an organic layer located between them. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above.

[0005] Prior art literature

[0006] Patent Literature

[0007] (Patent Document 1) Korean Patent Publication No. 2000-0051826 Summary of the invention

[0008] Technical issues

[0009] The present specification provides a compound and an organic light-emitting device including the same.

[0010] Solution to the problem

[0011] One embodiment of the present specification provides a compound of the following Chemical Formula 1.

[0012] [Chemical formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] One to four of R1 to R10 are combined with the following chemical formula 2,

[0016] The remaining R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0017] [Chemical formula 2]

[0018]

[0019] In the above chemical formula 2,

[0020] X is O or S,

[0021] L1 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted heteroarylene group,

[0022] Any one of R11 to R14 is a moiety that binds to L1,

[0023] The remaining R11 to R14 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0024] R15 to R17 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0025] l1 is an integer from 1 to 4. When l1 is 2 or more, the two or more L1s are the same or different from each other. n is an integer of 1 or 2. When n is 2, the structures in the brackets are the same or different from each other.

[0026] * is a portion bonded to the above chemical formula 1.

[0027] In addition, one embodiment of the present specification provides an organic light-emitting device, which includes: a first electrode; a second electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contains the above-mentioned compound.

[0028] In addition, one embodiment of the present specification provides an organic light-emitting device, which includes: a first electrode; a second electrode; a first light-emitting layer arranged between the first electrode and the second electrode; and a second light-emitting layer arranged between the first light-emitting layer and the second electrode, the first light-emitting layer contains the compound of the above chemical formula 1, and the second light-emitting layer contains the compound of the following chemical formula 5.

[0029] [Chemical formula 5]

[0030]

[0031] In the above chemical formula 5,

[0032] L20 and L21 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0033] Ar20 and Ar21 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0034] R301 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0035] r301 is an integer of 1 to 8. When r301 is 2 or more, two or more R301s may be the same as or different from each other.

[0036] Effects of the Invention

[0037] The compound according to one embodiment of the present specification is used in an organic light-emitting device, which can reduce the driving voltage of the organic light-emitting device and improve the efficiency. In addition, the thermal stability of the compound can be used to improve the life characteristics of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] Figures 1 to 4 Examples of organic light emitting devices according to several embodiments of the present specification are illustrated.

[0039] Figure 5 This is a diagram showing the MS chart of compound A.

[0040] Explanation of symbols

[0041] 1: Substrate

[0042] 2: First electrode

[0043] 3: Second electrode

[0044] 4: Luminous layer

[0045] 4-1: The first light-emitting layer

[0046] 4-2: Second light-emitting layer

[0047] 5: Hole injection layer

[0048] 6: Hole transport layer

[0049] 7: Electron transport layer

[0050] 8: Electron injection layer DETAILED DESCRIPTION

[0051] One embodiment of the present specification provides the compound of the above Chemical Formula 1.

[0052] The compound of Chemical Formula 1 according to one embodiment of the present specification is a pyrene-based compound substituted with Chemical Formula 2. The compound of Chemical Formula 1 includes pyrene and Chemical Formula 2, thereby improving the injection, transport, and regulation properties of holes and electrons, and improving the recombination efficiency of electrons and holes in the light-emitting layer.

[0053] Below, the terms used in this specification are explained in more detail to facilitate understanding.

[0054] In the present specification, when it is indicated that a certain part “includes / comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0055] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0056] In this specification, the above-mentioned "layer" is interchangeable with the "film" mainly used in this technical field, and refers to a coating covering the target area. The size of the above-mentioned "layer" is not limited, and the sizes of each "layer" can be the same or different. In one embodiment, the size of the "layer" can be equal to the size of the entire device, can be equivalent to the size of a specific functional area, or can be as small as a single sub-pixel.

[0057] In this specification, "or / or" means inclusive "or / or" rather than exclusive "or / or". For example, it means that condition A or B satisfies any of the following: A is true (or exists), B is false (or does not exist); and A is false (or does not exist), B is true (or exists); and A and B are both true (or exist).

[0058] In this specification, the meaning of specific substance A contained in layer B includes both i) the case where one or more substances A are contained in one layer B and ii) the case where layer B is composed of one or more layers and substance A is contained in one or more of the multiple layers B.

[0059] In this specification, the meaning of a specific substance A being contained in layer C or layer D refers to all of the following situations: substance A i) is contained in one or more layers among one or more layers C, or ii) is contained in one or more layers among one or more layers D, or iii) is contained in one or more layers C and one or more layers D, respectively.

[0060] In the present invention, "*" and Each represents a site for connection with other substituents or a bonding portion.

[0061] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0062] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, a halogen group, a nitrile group (-CN), a nitro group, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, a phosphine oxide group, an aryloxy group, an alkylthio group, Arylthio Alkylsulfonyl Arylsulfonyl The alkylene group may be substituted with one or more substituents selected from the group consisting of alkenyl, silyl, boronyl, amine, aryl, and heterocyclic groups, or may be substituted with a substituent formed by connecting two or more substituents selected from the group consisting of the above-mentioned substituents, or may not have any substituent. For example, the "substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent formed by connecting two phenyl groups.

[0063] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an aryloxy group, an alkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0064] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, alkyl, aryl, and heterocyclic groups, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0065] In this specification, two or more substituents are linked to each other, which means that the hydrogen of any substituent is linked to another substituent. For example, two substituents can be linked to each other to form a phenyl group and a naphthyl group. In addition, the three substituents connected include not only (substituent 1)-(substituent 2)-(substituent 3) connected continuously, but also (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl and isopropyl can be connected to form The above definition also applies to 4 or more substituents connected together.

[0066] Examples of the above substituents are described below, but are not limited thereto.

[0067] In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0068] In the present specification, the silyl group can be represented by the chemical formula -SiYaYbYc, wherein Ya, Yb and Yc can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0069] In this specification, the boron group can be represented by the chemical formula -BYdYe, and the above-mentioned Yd and Ye can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The above-mentioned boron group specifically includes trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but is not limited thereto.

[0070] In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. In one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. In another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. In another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0071] In this specification, the alkoxy group can be straight chain, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 20. Specifically, it can be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, an isopropyloxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, etc., but it is not limited thereto.

[0072] The alkyl group, alkoxy group, and other substituents containing an alkyl portion described in the present specification include all of linear and branched forms.

[0073] In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but preferably 2 to 40. In one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. In another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. In another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are 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-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0074] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0075] In the present specification, the amino group is -NH2, and the above-mentioned amino group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the above-mentioned substituted amino group is not particularly limited, but is preferably 1 to 30. In one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 20. In one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 10. As specific examples of substituted amino groups, there are methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthracenylamino, dibenzofuranylphenylamino, 9-methylanthrylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, diphenylamino, etc., but are not limited thereto.

[0076] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. In one embodiment, the carbon number of the aryl group is 6 to 30. In one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, phenylene, fluorenyl, triphenylene, etc., but are not limited to these.

[0077] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

[0078] When the fluorenyl group is substituted, it may be Isospirofluorenyl; (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and the like substituted fluorenyl, but the present invention is not limited thereto.

[0079] In the present specification, the above description on the aryl group can be applied to the aryl group in the aryloxy group.

[0080] In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. In one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. In one embodiment, the number of carbon atoms of the heterocyclic group is 3 to 30. In one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarbazolyl, triazinyl and the like, but are not limited thereto.

[0081] In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.

[0082] Next, the compound of the above Chemical Formula 1 will be described in detail.

[0083] In one embodiment of the present specification, the above n is 1.

[0084] In one embodiment of the present specification, the above n is 2.

[0085] In one embodiment of the present specification, any one of R11 to R14 in the above Chemical Formula 2 is bonded to L1.

[0086] In the present specification, "the rest of R11 to R14" refers to the part of the above-mentioned R11 to R14 that is not bonded to L1.

[0087] In one embodiment of the present specification, the above Chemical Formula 2 is any one of the following Chemical Formulas 2-1 to 2-4.

[0088] [Chemical formula 2-1]

[0089]

[0090] [Chemical formula 2-2]

[0091]

[0092] [Chemical formula 2-3]

[0093]

[0094] [Chemical formula 2-4]

[0095]

[0096] In the above chemical formulas 2-1 to 2-4,

[0097] *, X, L1 and l1 are the same as those in the above chemical formula 2,

[0098] R11 to R17 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0099] In one embodiment of the present specification, the above l1 is 1.

[0100] In one embodiment of the present specification, the above Chemical Formula 2 is any one of the following Chemical Formulas 2-5 to 2-8.

[0101] [Chemical formula 2-5]

[0102]

[0103] [Chemical formula 2-6]

[0104]

[0105] [Chemical formula 2-7]

[0106]

[0107] [Chemical formula 2-8]

[0108]

[0109] In the above chemical formulas 2-5 to 2-8,

[0110] *, X and L1 are the same as those defined in the above chemical formula 2,

[0111] X' is O or S,

[0112] R11 to R17 and R11′ to R17′ are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0113] In one embodiment of the present specification, any one of the above R11 to R14 is a portion bonded to L1, and the remaining R11 to R14 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted silyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0114] In one embodiment of the present specification, any one of R11 to R14 is a portion bonding to L1, and the remaining R11 to R14 are the same as or different from each other and are independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0115] In one embodiment of the present specification, any one of R11 to R14 is a portion that binds to L1, and the remaining R11 to R14 are the same as or different from each other and are independently hydrogen or deuterium.

[0116] In one embodiment of the present specification, R11 to R14 in the above chemical formulas 2-1 to 2-4 are the same as or different from each other, and are each 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.

[0117] In one embodiment of the present specification, R11 to R14 in the above Chemical Formulae 2-1 to 2-4 are the same as or different from each other, and are independently hydrogen or deuterium.

[0118] In one embodiment of the present specification, R11 to R14 and R11' to R14' in the above chemical formulas 2-5 to 2-8 are the same as or different from each other, and are each 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.

[0119] In one embodiment of the present specification, R11 to R14 and R11′ to R14′ in the above Chemical Formulae 2-5 to 2-8 are the same as or different from each other, and are independently hydrogen or deuterium.

[0120] In one embodiment of the present specification, the Chemical Formula 2 is any one of the Chemical Formulas 2-1 to 2-8.

[0121] In one embodiment of the present specification, the above R15 to R17 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted silyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0122] In one embodiment of the present specification, R15 to R17 are the same as or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0123] In one embodiment of the present specification, R15 to R17 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0124] In one embodiment of the present specification, R15 and R17 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0125] In one embodiment of the present specification, the above R16 is a substituted or unsubstituted aryl group.

[0126] In one embodiment of the present specification, the above R16 is an aryl group which may be substituted by deuterium.

[0127] In one embodiment of the present specification, the above R16 is a substituted or unsubstituted phenyl group.

[0128] In one embodiment of the present specification, the above R16 is a phenyl group which may be substituted with deuterium.

[0129] In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted heteroarylene group.

[0130] In one embodiment of the present specification, L1 is a direct bond; a phenylene group which is substituted or unsubstituted by one or more substituents selected from deuterium, an alkyl group, an aryl group, and a heterocyclic group; a biphenylene group which is substituted or unsubstituted by one or more substituents selected from deuterium, an alkyl group, an aryl group, and a heterocyclic group; a naphthylene group which is substituted or unsubstituted by one or more substituents selected from deuterium, an alkyl group, an aryl group, and a heterocyclic group; or a heteroarylene group which is substituted or unsubstituted by one or more substituents selected from deuterium, an alkyl group, an aryl group, and a heterocyclic group.

[0131] In one embodiment of the present specification, L1 is a direct bond, a phenylene group which is substituted or unsubstituted with one or more substituents selected from deuterium and an aryl group, a biphenylene group which is substituted or unsubstituted with one or more substituents selected from deuterium and an aryl group, a naphthylene group which is substituted or unsubstituted with one or more substituents selected from deuterium and an aryl group, or a heteroarylene group which is substituted or unsubstituted with one or more substituents selected from deuterium and an aryl group.

[0132] In one embodiment of the present specification, the above-mentioned L1 is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0133] In one embodiment of the present specification, L1 is a direct bond, a phenylene group which may be substituted by one or more substituents selected from deuterium and an aryl group, or a biphenylene group which may be substituted by one or more substituents selected from deuterium and an aryl group.

[0134] In one embodiment of the present specification, one or two of the above R1 to R10 are combined with the above Chemical Formula 2, and the remaining R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0135] In one embodiment of the present specification, one of the above R1 to R10 is bonded to the above Chemical Formula 2.

[0136] In one embodiment of the present specification, two of the above R1 to R10 are combined with the above Chemical Formula 2.

[0137] In one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-3.

[0138] [Chemical formula 1-1]

[0139]

[0140] [Chemical formula 1-2]

[0141]

[0142] [Chemical formula 1-3]

[0143]

[0144] In the above chemical formulas 1-1 to 1-3,

[0145] R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0146] It is a part combined with the above chemical formula 2.

[0147] In one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-11 to 1-15.

[0148] [Chemical formula 1-11]

[0149]

[0150] [Chemical formula 1-12]

[0151]

[0152] [Chemical formula 1-13]

[0153]

[0154] [Chemical formula 1-14]

[0155]

[0156] [Chemical formula 1-15]

[0157]

[0158] In the above chemical formulas 1-11 to 1-15,

[0159] R2 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0160] It is a part combined with the above chemical formula 2.

[0161] In one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-21 to 1-27.

[0162] [Chemical formula 1-21]

[0163]

[0164] [Chemical formula 1-22]

[0165]

[0166] [Chemical formula 1-23]

[0167]

[0168] [Chemical formula 1-24]

[0169]

[0170] [Chemical formula 1-25]

[0171]

[0172] [Chemical formula 1-26]

[0173]

[0174] [Chemical formula 1-27]

[0175]

[0176] In the above chemical formulas 1-21 to 1-27,

[0177] R1 and R3 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0178] It is a part combined with the above chemical formula 2.

[0179] In one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-31 to 1-33.

[0180] [Chemical formula 1-31]

[0181]

[0182] [Chemical formula 1-32]

[0183]

[0184] [Chemical formula 1-33]

[0185]

[0186] In the above Chemical Formulas 1-31 to 1-33,

[0187] R1, R2, and R4 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0188] It is a part combined with the above chemical formula 2.

[0189] In the present specification, “the rest of R1 to R10” refers to the portion of the above R1 to R10 that is not bonded to Chemical Formula 2.

[0190] In one embodiment of the present specification, 1 to 4 of the above R1 to R10 are combined with the above Chemical Formula 2, and the remaining R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted silyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0191] In one embodiment of the present specification, 1 to 4 of the above R1 to R10 are combined with the above Chemical Formula 2, and the remaining R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0192] In one embodiment of the present specification, 1 to 4 of the above R1 to R10 are combined with the above Chemical Formula 2, and the remaining R1 to R10 are the same as or different from each other and are independently hydrogen; deuterium; aryl group substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic group; or heterocyclic group substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic group.

[0193] In one embodiment of the present specification, 1 to 4 of the above R1 to R10 are combined with the above Chemical Formula 2, and the remaining R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, an aryl group which may be substituted or unsubstituted with one or more substituents selected from deuterium and an aryl group, or a heterocyclic group which may be substituted or unsubstituted with one or more substituents selected from deuterium and an aryl group.

[0194] In one embodiment of the present specification, 1 to 4 of the above R1 to R10 are combined with the above Chemical Formula 2, and the remaining R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0195] In one embodiment of the present specification, 1 to 4 of the above R1 to R10 are combined with the above Chemical Formula 2, and the remaining R1 to R10 are the same or different from each other and are independently hydrogen; deuterium; phenyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic groups; biphenyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic groups; terphenyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic groups; naphthyl substituted or unsubstituted by one or more substituents selected from alkyl, aryl and heterocyclic group; phenanthrenyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic group; pyrenyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic group; dibenzofuranyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic group; or dibenzothiophenyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic group.

[0196] In one embodiment of the present specification, 1 to 4 of the above R1 to R10 are combined with the above Chemical Formula 2, and the remaining R1 to R10 are the same as or different from each other and are independently hydrogen; deuterium; phenyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic groups; biphenyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic groups; naphthyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic groups; pyrenyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic groups; or dibenzofuranyl substituted or unsubstituted by one or more substituents selected from deuterium, alkyl, aryl and heterocyclic groups.

[0197] In one embodiment of the present specification, one or two of the above R1 to R10 are combined with the above Chemical Formula 2, and the remaining R1 to R10 are the same as or different from each other and are each independently hydrogen, deuterium, phenyl substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups, biphenyl substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups, naphthyl substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups, pyrenyl substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups, or dibenzofuranyl substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups.

[0198] In one embodiment of the present specification, the compound of the above Chemical Formula 1 may or may not contain deuterium.

[0199] In one embodiment of the present specification, the compound of the above Chemical Formula 1 contains at least one deuterium.

[0200] The compound of the above chemical formula 1 has the following effects by containing deuterium. The physical and chemical properties such as the bond length of the chemical bond related to deuterium are different from those of hydrogen. Compared with the CH bond, the stretching amplitude of the CD bond is smaller, so the van der Waals radius of deuterium is smaller than that of hydrogen. In addition, under normal circumstances, it can be shown that the CD bond is shorter and stronger than the CH bond. Therefore, when the hydrogen at the substitutable position of the above chemical formula 1 is replaced by deuterium, the energy of the ground state is reduced, the bond length of deuterium and carbon becomes shorter, and thus the molecular hardcore volume is reduced, so the electrical polarizability can be reduced, and the intermolecular interaction is weakened, thereby increasing the film volume. In addition, such characteristics can produce the effect of reducing the crystallinity of the film, that is, an amorphous state. In addition, such characteristics can effectively improve the lifespan and driving characteristics of organic light-emitting devices, and the heat resistance can be further improved compared with existing organic light-emitting devices.

[0201] In one embodiment of the present specification, the deuterium substitution rate of the compound of the above Chemical Formula 1 is 10% or more.

[0202] In one embodiment of the present specification, the deuterium substitution rate of the compound of the above Chemical Formula 1 is 20% or more.

[0203] In one embodiment of the present specification, the deuterium substitution rate of the compound of the above Chemical Formula 1 is 30% or more.

[0204] In one embodiment of the present specification, the deuterium substitution rate of the compound of the above Chemical Formula 1 is 40% or more.

[0205] In one embodiment of the present specification, the upper limit of the deuterium substitution rate of the compound of the above Chemical Formula 1 is not limited, but may be, for example, 100% or less or less than 100%.

[0206] As an example, the deuterium substitution rate of the above Chemical Formula 1 is 10% to 100%.

[0207] In the present specification, “containing deuterium”, “deuterated” or “deuterated” means that hydrogen at a substitutable position of the compound is substituted with deuterium.

[0208] In the present specification, “overdeuterated” refers to a compound or group in which all hydrogen in the molecule is replaced by deuterium, and has the same meaning as “100% deuterated”.

[0209] In the present specification, "X% deuterated", "deuteration degree X%" or "deuterium substitution rate X%" means that X% of the hydrogen atoms at substitutable positions in the structure are substituted with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" the dibenzofuran, "deuteration degree 25%" of the dibenzofuran or "deuterium substitution rate 25%" of the dibenzofuran means that 2 of the 8 hydrogen atoms at substitutable positions of the dibenzofuran are substituted with deuterium.

[0210] In this specification, the "degree of deuteration" or "deuterium substitution rate" can be determined by nuclear magnetic resonance spectroscopy ( 1 The expression of the peptides can be confirmed by known methods such as H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry) or GC / MS (Gas Chromatography / Mass Spectrometry).

[0211] Specifically, by nuclear magnetic resonance spectroscopy ( 1 When analyzing the "deuteration degree" or "deuterium substitution rate" by H NMR, DMF (dimethylformamide) can be added as an internal standard. 1 The integration ratio on H NMR is used to calculate the deuteration degree or deuterium substitution rate from the integrated amount of the total peak.

[0212] In addition, when analyzing the "degree of deuteration" or "deuterium substitution rate" by TLC / MS (thin layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the distribution formed by the molecular weight at the end of the reaction. For example, when analyzing the degree of deuteration of the following compound A, the molecular weight of the following starting material is 506. When it is indicated that Figure 5 When the maximum molecular weight (median value) of the following compound A in the MS chart is 527, 21 of the 26 hydrogen atoms at the substitutable positions of the following starting material are substituted with deuterium, and therefore it can be calculated that about 81% of the hydrogen atoms are deuterated.

[0213]

[0214] In this specification, D represents deuterium.

[0215] In one embodiment of the present specification, the compound is any one of the following structures.

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225] In one embodiment of the present specification, the band gap of the compound of the above Chemical Formula 1 is 2.9 eV or more.

[0226] In one embodiment of the present specification, the band gap of the compound of Chemical Formula 1 is 2.9 eV to 4.0 eV.

[0227] The organic compound used in the organic light-emitting device must have a band gap of 0.5eV to 4.0eV to play the role of an organic semiconductor, and in order to display blue, a band gap energy of at least 2.9eV is required. According to the fluorescent blue light-emitting principle of the host-dopant system, the band gap of the blue fluorescent host must be greater than the band gap of the blue fluorescent dopant in order for energy transfer to occur smoothly. Therefore, the blue fluorescent host preferably has an energy band gap of 2.9eV to 4.0eV.

[0228] In this specification, "energy level" refers to the magnitude of energy. Therefore, the energy level is interpreted as representing the absolute value of the energy value. For example, the low or deep energy level means that the absolute value increases from the vacuum energy level to the negative direction.

[0229] In this specification, HOMO (highest occupied molecular orbital) refers to the molecular orbital function (highest occupied molecular orbital) of the electron in the region with the highest energy in the region that can participate in the bonding, LUMO (lowest unoccupied molecular orbital) refers to the molecular orbital function (lowest unoccupied molecular orbital) of the electron in the antibonding region with the lowest energy, and the HOMO energy level refers to the distance from the vacuum energy level to the HOMO. In addition, the LUMO energy level refers to the distance from the vacuum energy level to the LUMO.

[0230] In this specification, the HOMO level can be measured by using a photoelectron spectrometer (AC3 manufactured by Riken Keiki Co., Ltd.) under atmospheric pressure, and the LUMO level can be calculated using a wavelength value measured by photoluminescence (PL).

[0231] In this specification, the band gap refers to the difference between the HOMO energy level and the LUMO energy level.

[0232] Next, an organic light-emitting device including the above-mentioned compound will be described in detail.

[0233] The present specification provides an organic light-emitting device, comprising: a first electrode; a second electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound represented by the chemical formula 1.

[0234] The organic layer of the organic light-emitting device of the present specification may be formed of a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, it may have a structure including two or more layers of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

[0235] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0236] In one embodiment of the present specification, the organic layer includes a light-emitting layer.

[0237] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant.

[0238] In one embodiment of the present specification, the host material includes fused and / or unfused aromatic ring derivatives or heterocyclic compounds. Specifically, aromatic fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0239] In one embodiment of the present specification, the host includes the compound of the above Chemical Formula 1, but is not limited thereto.

[0240] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

[0241] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as a main component of the light-emitting layer.

[0242] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant in a weight ratio of 0.1:99.9 to 20:80.

[0243] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the host includes the compound represented by Chemical Formula 1.

[0244] In one embodiment of the present specification, the dopant is a blue dopant.

[0245] In one embodiment of the present specification, the dopant material includes aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamine groups, including pyrene, anthracene, In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamine. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0246] In one embodiment of the present specification, the light-emitting layer includes a dopant, and the dopant includes a fluorescent dopant.

[0247] In one embodiment of the present specification, the fluorescent dopant includes one or more selected from pyrene-based compounds and non-pyrene-based compounds.

[0248] In one embodiment of the present specification, the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound.

[0249] The above-mentioned pyrene-based compounds and non-pyrene-based compounds may be used without limitation as long as they are compounds used in the art.

[0250] In one embodiment of the present specification, the fluorescent dopant is a phenanthrene-based compound.

[0251] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes the compound represented by the above Chemical Formula 1, and the dopant includes one or more selected from pyrene-based compounds and non-pyrene-based compounds.

[0252] In one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes the compound represented by the above Chemical Formula 1, and the dopant includes a non-pyrene compound.

[0253] In one embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.

[0254] In one embodiment of the present specification, the boron-based compound is represented by the following chemical formula DB.

[0255] [Chemical Formula DB]

[0256]

[0257] In the above chemical formula DB,

[0258] R g1 To R g5 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted amine, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0259] rg' and rg" are each an integer of 1 to 4, rg"' is an integer of 1 to 3, and when rg', rg" and rg"' are 2 or more, the substituents in the respective brackets are the same as or different from each other.

[0260] In one embodiment of the present specification, the above R g1 To R g5 They are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted amino group having 1 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 heteroaryl group having 2 to 30 carbon atoms.

[0261] In one embodiment of the present specification, the above R g1 To R g5 The same as or different from each other, and each independently is a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0262] In one embodiment of the present specification, the above R g1 To R g5 The same as or different from each other, and each independently represents an amino group which may be substituted by an aryl group, an alkyl group, or an aryl group which may be substituted by an alkyl group.

[0263] In one embodiment of the present specification, the above R g1 To R g5The same as or different from each other, and each independently represents an amine group substituted by an aryl group, a linear or branched alkyl group, or an aryl group substituted or unsubstituted by a linear or branched alkyl group.

[0264] In one embodiment of the present specification, the above R g1 and R g2 The same as or different from each other, and each independently is a substituted or unsubstituted aryl group.

[0265] In one embodiment of the present specification, the above R g1 and R g2 The same as or different from each other, and each independently is an aryl group which may be substituted by an alkyl group.

[0266] In one embodiment of the present specification, the above R g1 and R g2 The same as or different from each other, and each independently is an aryl group substituted by an alkyl group.

[0267] In one embodiment of the present specification, the above R g1 and R g2 The same as or different from each other, and each independently represents a phenyl group substituted by a branched alkyl group having 4 to 30 carbon atoms.

[0268] In one embodiment of the present specification, the above R g3 To R g5 The same as or different from each other, and each independently represents a substituted or unsubstituted amino group, or a substituted or unsubstituted alkyl group.

[0269] In one embodiment of the present specification, the above R g3 To R g5 The same as or different from each other, and each independently represents an amino group which may be substituted with an aryl group, or an alkyl group.

[0270] In one embodiment of the present specification, the above R g3 To R g5 The same as or different from each other, and each independently represents an amino group substituted with an aryl group, or a linear or branched alkyl group.

[0271] In one embodiment of the present specification, the above R g3 and R g4 The same as or different from each other, and each independently is a substituted or unsubstituted alkyl group.

[0272] In one embodiment of the present specification, the above R g3 and R g4 The same as or different from each other, and each independently is an alkyl group.

[0273] In one embodiment of the present specification, the above R g5 is a substituted or unsubstituted amine group.

[0274] In one embodiment of the present specification, the above R g5 It is an amine group substituted by an aromatic group.

[0275] In one embodiment of the present specification, the chemical formula DB has the following structure.

[0276]

[0277] In one embodiment of the present specification, the organic light-emitting device is a blue organic light-emitting device.

[0278] In one embodiment of the present specification, the light-emitting layer further includes one or more hosts different from the compound of Chemical Formula 1. That is, the light-emitting layer includes two or more mixed hosts, and one or more of the two or more mixed hosts includes the compound represented by Chemical Formula 1.

[0279] The host different from the compound of the above Chemical Formula 1 can be used without limitation as long as it is different from the above Chemical Formula 1. For example, it can be a compound containing anthracene, but is not limited thereto.

[0280] In one embodiment of the present specification, another light-emitting layer is further included between the light-emitting layer and the second electrode.

[0281] In one embodiment of the present specification, the light-emitting layer has two or more layers, and one or more layers of the two or more light-emitting layers contain the compound of Chemical Formula 1.

[0282] In one embodiment of the present specification, the organic light-emitting device includes two light-emitting layers (bilayer).

[0283] In one embodiment of the present specification, the light-emitting layer includes two layers, and one of the two light-emitting layers includes the compound of Chemical Formula 1.

[0284] One embodiment of the present specification provides an organic light-emitting device, which includes: a first electrode; a second electrode; a first light-emitting layer arranged between the first electrode and the second electrode; and a second light-emitting layer arranged between the first light-emitting layer and the second electrode, the first light-emitting layer contains the compound of the above chemical formula 1, and the second light-emitting layer contains the compound of the following chemical formula 5.

[0285] [Chemical formula 5]

[0286]

[0287] In the above chemical formula 5,

[0288] L20 and L21 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0289] Ar20 and Ar21 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0290] R301 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0291] r301 is an integer of 1 to 8. When r301 is 2 or more, two or more R301s may be the same as or different from each other.

[0292] In one embodiment of the present specification, the first light-emitting layer includes the compound of Chemical Formula 1 as a host.

[0293] In one embodiment of the present specification, the second light-emitting layer includes the compound of Chemical Formula 5 as a host.

[0294] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a directly bonded or substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0295] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0296] In one embodiment of the present specification, each of L20 and L21 is a direct bond.

[0297] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0298] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0299] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

[0300] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0301] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a substituted or unsubstituted naphthyl group.

[0302] In one embodiment of the present specification, each of Ar20 and Ar21 is a naphthyl group.

[0303] In one embodiment of the present specification, the above R301 is hydrogen or deuterium.

[0304] In one embodiment of the present specification, the chemical formula 5 has the following structure.

[0305]

[0306] In one embodiment of the present specification, the first light-emitting layer and the second light-emitting layer are arranged in contact with each other. Thus, singlet light is emitted in the first light-emitting layer, and TTF light is emitted in the second light-emitting layer. The overlapping area between the singlet light-emitting area and the TTF light-emitting area is reduced, thereby suppressing the reduction of TTF efficiency caused by the collision between triplet excitons and carriers.

[0307] In one embodiment of the present specification, the thickness of the first light-emitting layer is 5 nm to 500 nm, specifically 5 nm to 300 nm, or 5 nm to 150 nm.

[0308] In one embodiment of the present specification, the thickness of the second light-emitting layer is 5 nm to 500 nm, specifically 5 nm to 300 nm, or 5 nm to 150 nm.

[0309] In one embodiment of the present specification, the maximum emission wavelength (λ 最大(max) ) is 400nm to 470nm. That is, the maximum emission wavelength of the emission spectrum of the organic light-emitting device is between 400nm and 470nm.

[0310] In one embodiment of the present specification, a covering layer is further provided on a surface opposite to a surface of at least one of the first electrode and the second electrode that faces the organic layer.

[0311] The above-mentioned covering layer is formed to prevent a large amount of light from being lost through total reflection of light in the organic light-emitting device. The covering layer has the property of fully protecting the lower cathode and light-emitting layer from external moisture penetration or contamination, and has a high refractive index, thereby preventing light loss caused by total reflection.

[0312] In one embodiment of the present specification, the cover layer may be provided on a surface opposite to a surface of the first electrode that faces the organic layer.

[0313] In one embodiment of the present specification, the cover layer may be provided on a surface opposite to a surface of the second electrode that faces the organic layer.

[0314] In one embodiment of the present specification, the cover layer may be provided on a surface opposite to a surface of the first electrode facing the organic layer and a surface opposite to a surface of the second electrode facing the organic layer.

[0315] In one embodiment of the present specification, as the above-mentioned covering layer, any material used in the technical field can be applied without limitation.

[0316] In one embodiment of the present specification, the organic light-emitting device 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, a hole blocking layer and an electron blocking layer.

[0317] In one embodiment of the present specification, the organic light-emitting device includes: a first electrode; a second electrode; a light-emitting layer arranged between the first electrode and the second electrode; and one or more organic layers arranged between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0318] In one embodiment of the present specification, one or more organic layers between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, can be selected from two or more of the group consisting of another light-emitting layer, a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer and an electron transport layer.

[0319] In one embodiment of the present specification, the first electrode is an anode or a cathode.

[0320] In one embodiment of the present specification, the second electrode is a cathode or an anode.

[0321] In one embodiment of the present specification, the organic light-emitting device may be a (normal type) organic light-emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0322] In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0323] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is shown in Figures 1 to 4 However, the structure of the organic light-emitting device of the present invention is not limited to Figures 1 to 3 .

[0324] Figure 1 exemplifies the structure of an organic light-emitting device in which a first electrode 2, a light-emitting layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The above-mentioned compound is contained in the light-emitting layer.

[0325] Figure 2 exemplifies the structure of an organic light-emitting device in which a first electrode 2, a first light-emitting layer 4-1, a second light-emitting layer 4-2, and a second electrode 3 are sequentially stacked on a substrate 1. The above-mentioned compound is contained in the light-emitting layer.

[0326] Figure 3 exemplifies 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 transport layer 7 , an electron injection layer 8 and a second electrode 3 are sequentially stacked on a substrate 1 .

[0327] Figure 4 The structure of an organic light-emitting device is illustrated in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, a first light-emitting layer 4-1, a second light-emitting layer 4-2, an electron transport layer 7, an electron injection layer 8 and a second electrode 3 are sequentially stacked on a substrate 1.

[0328] The organic light-emitting device of the present specification can be manufactured by materials and methods known in the art, except that the light-emitting layer, the first light-emitting layer and / or the second light-emitting layer include the above compound, ie, the compound of the above Chemical Formula 1.

[0329] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the device can be manufactured as follows: a metal or a conductive metal oxide or an alloy thereof is vapor-deposited on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, an organic layer including a light-emitting layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer.

[0330] In addition to this method, the organic light-emitting device can also be manufactured by sequentially vapor-depositing the second electrode material, the organic material layer, and the first electrode material on the substrate. However, the manufacturing method is not limited to this.

[0331] In one embodiment of the present specification, the compound of the chemical formula 1 can be used to form an organic layer by not only vacuum evaporation but also solution coating when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0332] As the first electrode, in order to smoothly inject holes into the organic layer, a material with a large work function is preferably used. For example, there are metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), 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-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but the present invention is not limited thereto.

[0333] As the second electrode, in order to facilitate electron injection into the organic layer, a material with a small work function is preferably used, for example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but not limited thereto.

[0334] The hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, has the effect of receiving holes from the anode, and has an excellent hole injection effect on the light-emitting layer or the light-emitting material. In addition, it is preferably a material that can prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. In addition, it is preferably a material with excellent thin film forming ability. In addition, it is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, and arylamine organics; hexanitrile hexaazatriphenylene organics; quinacridone organics; perylene organics; quinoxaline organics; anthraquinone, polyaniline, and polythiophene conductive polymers, etc., but are not limited to these.

[0335] In one embodiment of the present specification, a quinoxaline-based organic substance is used for the hole injection layer.

[0336] In one embodiment of the present specification, the hole injection layer includes a compound of the following chemical formula HI-A.

[0337] [Chemical formula HI-A]

[0338]

[0339] In the above chemical formula HI-A,

[0340] R h1 To R h6 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted amine, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0341] In one embodiment of the present specification, the above R h1 To R h6 At least one of them is a cyano group.

[0342] In one embodiment of the present specification, the above R h1 To R h6 Each is a cyano group.

[0343] In one embodiment of the present specification, the chemical formula HI-A is the following structure.

[0344]

[0345] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, preferably a material with a large mobility for holes. As specific examples of hole transport materials, there are arylamine organics, carbazole organics, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto. Specifically, arylamine organics or carbazole organics are used in the hole transport layer.

[0346] In one embodiment of the present specification, the hole transport layer includes a compound of the following chemical formula HT-A.

[0347] [Chemical formula HT-A]

[0348]

[0349] In the above chemical formula HT-A,

[0350] L i1 is a substituted or unsubstituted arylene group,

[0351] R i1 To R i4 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted amine, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0352] li1 is an integer of 1 to 5. When li1 is 2 or more, two or more Li1s are the same as or different from each other.

[0353] In one embodiment of the present specification, the above R i1 To R i4 The same as or different from each other, and each independently is a substituted or unsubstituted aryl group.

[0354] In one embodiment of the present specification, the above R i1 To R i4 The same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

[0355] In one embodiment of the present specification, the above L i1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group.

[0356] In one embodiment of the present specification, the chemical formula HT-A is the following structure.

[0357]

[0358] In one embodiment of the present specification, the hole transport layer includes a compound of the following chemical formula HT-B.

[0359] [Chemical formula HT-B]

[0360]

[0361] In the above chemical formula HT-B,

[0362] L i2 is a substituted or unsubstituted arylene group,

[0363] R i5 To R i8 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted amine, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0364] Li2 is an integer from 1 to 5. When Li2 is 2 or more, the two or more Li2 are the same or different from each other.

[0365] i5 and i6 are each an integer of 1 to 4. When i5 and i6 are 2 or more, the substituents in the respective brackets are the same as or different from each other.

[0366] In one embodiment of the present specification, the above Ri5 To R i8 are the same as or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0367] In one embodiment of the present specification, the above R i5 and R i6 Each is hydrogen.

[0368] In one embodiment of the present specification, the above R i7 and R i8 The same as or different from each other, and each independently is a substituted or unsubstituted aryl group.

[0369] In one embodiment of the present specification, the above R i7 and R i8 The same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

[0370] In one embodiment of the present specification, the above L i2 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group.

[0371] In one embodiment of the present specification, the chemical formula HT-B has the following structure.

[0372]

[0373] In one embodiment of the present specification, the hole transport layer includes at least one of the compound of the chemical formula HT-A and the compound of the chemical formula HT-B.

[0374] The hole regulating layer is a layer that regulates the holes transferred from the hole transport layer to be smoothly injected into the light-emitting layer, and prevents the electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer, thereby improving the life and efficiency of the device. The hole regulating 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 performs hole injection and hole transport.

[0375] The electron regulating layer is a layer for regulating the smooth injection of electrons transferred from the electron transporting layer into the light emitting layer, and any known material can be used without limitation.

[0376] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, and a material with a large electron mobility is suitable. Specific examples of the electron transport material include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, benzimidazole compounds, organic free radical compounds, metal coordination compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto.

[0377] Examples of the metal coordination compounds include 8-hydroxyquinoline lithium (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) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but the present invention is not limited thereto.

[0378] The above-mentioned electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, suitable cathode materials are conventional materials with a low work function and accompanied by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., and in each case accompanied by an aluminum layer or a silver layer.

[0379] In one embodiment of the present specification, the electron transport layer includes a benzimidazole compound.

[0380] In one embodiment of the present specification, the electron transport layer includes a compound of the following chemical formula ET-1.

[0381] [Chemical formula ET-1]

[0382]

[0383] In the above chemical formula ET-1,

[0384] L601 to L603 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0385] Ar601 and Ar602 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0386] R601 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0387] In one embodiment of the present specification, L601 to L603 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted monocyclic arylene group, or a substituted or unsubstituted polycyclic arylene group.

[0388] In one embodiment of the present specification, L601 to L603 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

[0389] In one embodiment of the present specification, L601 and L602 are each directly bonded.

[0390] In one embodiment of the present specification, the above-mentioned L603 is a substituted or unsubstituted arylene group.

[0391] In one embodiment of the present specification, the above-mentioned L603 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

[0392] In one embodiment of the present specification, the above-mentioned L603 is a substituted or unsubstituted phenylene group.

[0393] In one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0394] In one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group, or a substituted or unsubstituted polycyclic aryl group.

[0395] In one embodiment of the present specification, the above-mentioned Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrene group, or a substituted or unsubstituted fluorenyl group.

[0396] In one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0397] In one embodiment of the present specification, each of Ar601 and Ar602 is a naphthyl group.

[0398] In one embodiment of the present specification, the above-mentioned R601 is a substituted or unsubstituted aryl group.

[0399] In one embodiment of the present specification, the above R601 is a substituted or unsubstituted phenyl group.

[0400] In one embodiment of the present specification, the above-mentioned R601 is a phenyl group.

[0401] In one embodiment of the present specification, the chemical formula ET-1 is the following structure.

[0402]

[0403] The electron injection layer is a layer that receives electrons from the electrode. As the electron injection material, the following materials are preferred: materials that have excellent ability to transport electrons, have the effect of receiving electrons from the second electrode, and have excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, materials that prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer and have excellent thin film forming ability are preferred. Specifically, there are metals, lithium fluoride (LiF), fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0404] In one embodiment of the present specification, the electron injection layer includes LiF.

[0405] The hole regulating layer, the electron regulating layer and the capping layer may be made of any known material without limitation.

[0406] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0407] The organic light-emitting device according to the present specification can be included in various electronic devices for use. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0408] Below, in order to specifically describe this specification, examples and comparative examples will be cited for detailed description. However, the examples and comparative examples of this specification can be deformed into various forms, and it is not interpreted that the scope of this specification is limited to the examples and comparative examples described in detail below. The examples and comparative examples of this specification are provided to more completely describe this specification to those skilled in the art.

[0409] Synthesis Example 1. Synthesis of Compound 1

[0410]

[0411] Synthesis Example 1-1. Synthesis of Intermediate 1-a

[0412] At room temperature, 2,4-dibromo-5-fluoroaniline (282 g, 1.05 mol) was dissolved in pyridine (167 g, 2.11 mol) and cooled to 10°C. Benzoyl chloride (178 g, 1.26 mol) was slowly added to the reaction mixture and refluxed for 1 hour. After the reaction solution was cooled, it was poured into distilled water (1 L) for extraction, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and intermediate 1-a (295 g, 0.79 mol) was obtained by column chromatography.

[0413] Synthesis Example 1-2. Synthesis of Intermediate 1-b

[0414] After dissolving the intermediate 1-a (295 g, 0.79 mol) in dimethylacetamide (DMAc) (2.3 L), copper iodide phenanthroline (CuI (phen)) (2.93 g, 0.01 mol) and potassium carbonate (K2CO3) (328 g, 2.37 mol) were added, the temperature was raised to 140°C, and refluxed with stirring for 24 hours. After the reaction solution was cooled, the solvent was removed under reduced pressure, and distilled water (1 L) was poured into it for extraction, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the intermediate 1-b (231 g, 0.79 mol) was obtained by column chromatography.

[0415] Synthesis Example 1-3. Synthesis of Intermediate 1-c

[0416] Intermediate 1-b (231 g, 0.79 mol), bis(pinacolato)diboron (PDB) (206 g, 0.81 mol), potassium acetate (KOAc) (199 g, 2.03 mol), bis(triphenylphosphine)palladium(II)diacetate (Pd(OAc)2(PCy3)2) (10.6 g, 0.0014 mol) were dissolved in xylene (1.7 L), heated to 120°C, and refluxed with stirring for 1 hour. The reaction solution was cooled, poured into distilled water (1 L) for extraction, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and intermediate 1-c (205 g, 0.70 mol) was obtained by column chromatography.

[0417]

[0418] Synthesis Example 1-4. Synthesis of Intermediate 1-d

[0419] After dissolving the intermediate 1-c (205 g, 0.60 mol), 2-bromo-3-chloro-1-phenol (138 g, 0.66 mol), sodium carbonate (Na2CO3) (160 g, 1.51 mol), and bis-(tri-tert-butylphosphine)palladium (BTP) (1.54 g, 0.003 mol) in tetrahydrofuran (THF) (2 L) and distilled water (1 L), the mixture was heated to 70°C and refluxed with stirring for 1 hour. After the reaction solution was cooled, distilled water (1 L) was added to generate a solid. The generated solid was filtered, dissolved in toluene, extracted several times, and the organic layer was dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, the next step of the reaction was carried out without additional separation process.

[0420] Synthesis Example 1-5. Synthesis of Intermediate 1-e

[0421] The intermediate 1-d mixture and K2CO3 (417g, 3.02mol) were dissolved in DMAc (1.3L), heated to 150°C, and refluxed for 2 hours. After the reaction solution was cooled, ethanol (3L) was added to generate a solid. The generated solid was dissolved in acetone, extracted several times, and the organic layer was dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, intermediate 1-e (169g, 0.53mol) was obtained by column chromatography.

[0422] Synthesis Example 1-6. Synthesis of Intermediate 1-f

[0423] The intermediate 1-e (50 g, 0.16 mol), 1-pyreneboronic acid (42.3 g, 0.17 mol), K2CO3 (43.2 g, 0.31 mol), bis(tri-tert-butylphosphine)palladium (0.39 g, 0.00078 mol) were dissolved in distilled water. After adding dioxane (500 mL) and distilled water (100 mL), the temperature was raised to 120°C and refluxed for 1 hour. After cooling the reaction solution, ethanol (500 mL) was poured into it to generate a solid. The generated solid was dissolved in toluene, extracted several times, and the organic layer was dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, intermediate 1-f (53 g, 0.11 mol) was obtained by column chromatography.

[0424] Synthesis Example 1-7. Synthesis of Intermediate 1-g

[0425] After dissolving the intermediate 1-f (53 g, 0.11 mol) and N-bromosuccinimide (NBS) (20.4 g, 0.11 mol) in dimethylformamide (DMF) (500 mL), the temperature was raised to 50°C and refluxed with stirring for 1 hour. After the reaction solution was cooled, a saturated aqueous solution of Na2S2O3 (300 mL) was added and refluxed with stirring for 30 minutes. The generated solid was filtered, dissolved in toluene, extracted several times, and the organic layer was dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the intermediate 1-g (58.9 g, 0.10 mol) was obtained by column chromatography.

[0426] Synthesis Example 1-8. Synthesis of Compound 1

[0427] The intermediate 1-g (58.9 g, 0.10 mol), phenylboronic acid (13.4 g, 0.11 mol), K2CO3 (41.46 g, 0.30 mol), bis(tri-tert-butylphosphine)palladium (0.25 g, 0.0005 mol) were dissolved in distilled water. After adding alkane (600mL) and distilled water (150mL), the temperature was raised to 120°C and refluxed for 1 hour. After the reaction solution was cooled, distilled water (1L) was added to generate a solid. The generated solid was filtered and dissolved in toluene. After extraction several times, the organic layer was dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, compound 1 (33.6g, 0.06mol) was obtained by column chromatography. [M+H + ]=561.2.

[0428] Synthesis Example 2. Synthesis of Compound 2

[0429]

[0430] In Synthesis Example 1-8, except that 1-naphthylboronic acid was used instead of the intermediate phenylboronic acid, the synthesis was carried out in the same manner as in Synthesis Example 1 to obtain Compound 2. [M+H + ]=612.3.

[0431] Synthesis Example 3. Synthesis of Compound 3

[0432]

[0433] Synthesis Example 3-1. Synthesis of Intermediate 3-a

[0434] Intermediate 3-a was obtained by the same method as in Synthesis Example 1-3 except that Intermediate 1-e was used instead of Intermediate 1-b.

[0435] Synthesis Example 3-2. Synthesis of Intermediate 3-b

[0436] Intermediate 3-a (40 g, 0.097 mol), 1-bromo-4-chlorobenzene (16.7 g, 0.087 mol), K3PO4 (41 g, 0.19 mol), tetrakis(triphenylphosphine)palladium (TTP) (1.12 g, 0.00097 mol) were dissolved in distilled water. After adding alkane (500 mL) and distilled water (100 mL), the temperature was raised to 120°C and refluxed for 1 hour. After the reaction solution was cooled, ethanol (500 mL) was added to generate a solid. The generated solid was filtered and dissolved in toluene. After extraction several times, the organic layer was dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, intermediate 3-b (26.95 g, 0.068 mol) was obtained by column chromatography.

[0437] Synthesis Example 3-3. Synthesis of Compound 3

[0438] Compound 3 was obtained by the same method as in Synthesis Example 1-6 except that Intermediate 3-b was used instead of Intermediate 1-e. [M+H + ]=562.2.

[0439] Synthesis Example 4. Synthesis of Compound 4

[0440]

[0441] Intermediate 3-a (30 g, 0.073 mol), 1-(5-chloro[1,1′-biphenyl]-3-yl)pyrene (25.5 g, 0.065 mol), K2CO3 (30.24 g, 0.22 mol), bis(tri-tert-butylphosphine)palladium (0.37 g, 0.00073 mol) were dissolved in distilled water. After adding alkane (600mL) and distilled water (150mL), the temperature was raised to 120°C and refluxed with stirring for 1 hour. After cooling the reaction solution, ethanol (500mL) was added to generate a solid. The generated solid was filtered and dissolved in toluene. After extraction several times, the organic layer was dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, compound 4 (37.2g, 0.058mol) was obtained by column chromatography. [M+H + ]=638.3.

[0442] Synthesis Example 5. Synthesis of Compound 5

[0443]

[0444] Synthesis Example 5-1. Synthesis of Intermediate 5-a

[0445] Intermediate 5-a was obtained by the same method as in Synthesis Example 1-4, except that 2-bromo-4-chloro-1-phenol was used instead of 2-bromo-3-chloro-1-phenol.

[0446] Synthesis Example 5-2. Synthesis of Intermediate 5-b

[0447] Intermediate 5-b was obtained by the same method as in Synthesis Example 1-5, except that Intermediate 5-a was used instead of Intermediate 1-d.

[0448] Synthesis Example 5-3. Synthesis of Intermediate 5-c

[0449] Intermediate 5-c was obtained by the same method as in Synthesis Example 1-6, except that Intermediate 5-b was used instead of Intermediate 1-e.

[0450] Synthesis Example 5-4. Synthesis of Intermediate 5-d

[0451] Intermediate 5-d was obtained by the same method as in Synthesis Example 1-7 except that Intermediate 5-c was used instead of Intermediate 1-f.

[0452] Synthesis Example 5-5. Synthesis of Compound 5

[0453] Compound 5 was obtained by the same method as in Synthesis Example 1-8 except that Intermediate 5-d was used instead of Intermediate 1-g. [M+H + ]=562.3

[0454] Synthesis Example 6. Synthesis of Compound 6

[0455]

[0456] Synthesis Example 6-1. Synthesis of Intermediate 6-a

[0457] Intermediate 6-a was obtained by the same method as in Synthesis Example 1-3 except that Intermediate 5-b was used instead of Intermediate 1-b.

[0458] Synthesis Example 6-2. Synthesis of Intermediate 6-b

[0459] Intermediate 6-b was obtained by the same method as in Synthesis Example 3-2 except that Intermediate 6-a was used instead of Intermediate 3-a and 1-bromo-3-chlorobenzene was used instead of 1-bromo-4-chlorobenzene.

[0460] Synthesis Example 6-3. Synthesis of Compound 6

[0461] Compound 6 was obtained by the same method as in Synthesis Example 1-6 except that Intermediate 6-b was used instead of Intermediate 1-e. [M+H + ]=562.3.

[0462] Synthesis Example 7. Synthesis of Compound 7

[0463]

[0464] Compound 7 was obtained by the same method as in Synthesis Example 4 except that Intermediate 6-a was used instead of Intermediate 3-a. + ]=638.2.

[0465] Synthesis Example 8. Synthesis of Compound 8

[0466]

[0467] In Synthesis Example 1-8, except that B-[4-(1-naphthalenyl)phenyl]boronic acid was used instead of phenylboronic acid, the same method as Synthesis Example 1-8 was used to obtain Compound 8. [M+H + ]=688.3.

[0468] Synthesis Example 9. Synthesis of Compound 9

[0469]

[0470] Synthesis Example 9-1. Synthesis of Intermediate 9-a

[0471] Intermediate 9-a was obtained by the same method as in Synthesis Example 1-4, except that 2-bromo-6-chloro-1-phenol was used instead of 2-bromo-3-chloro-1-phenol.

[0472] Synthesis Example 9-2. Synthesis of Intermediate 9-b

[0473] Intermediate 9-b was obtained by the same method as in Synthesis Example 1-5, except that Intermediate 9-a was used instead of Intermediate 1-d.

[0474] Synthesis Example 9-3. Synthesis of Compound 9

[0475] Compound 9 was obtained by the same method as in Synthesis Example 1-6 except that Intermediate 9-b was used instead of Intermediate 1-e. [M+H + ]=486.1.

[0476] Synthesis Example 10. Synthesis of Compound 10

[0477]

[0478] Synthesis Example 10-1. Synthesis of Intermediate 10-a

[0479] Intermediate 10-a was obtained by the same method as in Synthesis Example 1-3 except that Intermediate 9-b was used instead of Intermediate 1-b.

[0480] Synthesis Example 10-2. Synthesis of Compound 10

[0481] Compound 10 was obtained by the same method as in Synthesis Example 4 except that Intermediate 10-a was used instead of Intermediate 3-a. + ]=638.2.

[0482] Synthesis Example 11. Synthesis of Compound 11

[0483]

[0484] In Synthesis Example 1-6, except that 4-pyreneboronic acid was used instead of 1-pyreneboronic acid, the same method as Synthesis Example 1-6 was used to obtain Compound 11. [M+H + ]=486.2.

[0485] Synthesis Example 12. Synthesis of Compound 12

[0486]

[0487] In Synthesis Example 1-6, except that 2-pyreneboronic acid was used instead of 1-pyreneboronic acid, the same method as Synthesis Example 1-6 was used to obtain Compound 12. [M+H + ]=486.2.

[0488] Synthesis Example 13. Synthesis of Compound 13

[0489]

[0490] Synthesis Example 13-1. Synthesis of Intermediate 13-a

[0491] Pyrene-2,7-diyldiboronic acid (50 g, 0.17 mol), 1-bromo naphthalene (35.7 g, 0.17 mol), K2CO3 (47.67 g, 0.34 mol), bis(tri-tert-butylphosphine)palladium (0.44 g, 0.00086 mol) were dissolved in distilled water. After adding alkane (500 mL) and distilled water (100 mL), the temperature was raised to 120°C and refluxed for 1 hour. After cooling the reaction solution, ethanol (500 mL) was poured into it to generate a solid. The generated solid was dissolved in toluene, extracted several times, and the organic layer was dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, intermediate 13-a (44.9 g, 0.12 mol) was obtained by column chromatography.

[0492] Synthesis Example 13-2. Synthesis of Compound 13

[0493] Compound 13 was obtained by the same method as in Synthesis Example 1-6 except that Intermediate 13-a was used instead of 1-pyreneboronic acid. + ]=612.2.

[0494] Synthesis Example 14. Synthesis of Compound 14

[0495]

[0496] Compound 1 (20 g, 0.035 mol), D2O (28 g, 0.35 mol), trifluoromethanesulfonic anhydride (Tf2O) (98.7 g, 0.35 mol) were dissolved in trichlorobenzene (120 ml), and the temperature was raised to 140 ° C, and refluxed with stirring. After the reaction solution was cooled, the acid layer was removed, and it was extracted several times with a saturated aqueous solution of K2CO3. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and ethanol (500 ml) was added to generate a solid, which was filtered to obtain compound 14 (8.18 g, 0.014 mol). [M+H + ]=584.4.

[0497] Synthesis Example 15. Synthesis of Compound 15

[0498]

[0499] Compound 15 was obtained by the same method as in Synthesis Example 14 except that Compound 4 was used instead of Compound 1. + ]=664.4.

[0500] Example 1.

[0501] The glass substrate coated with ITO (indium tin oxide) as a film with a thickness of 150nm was placed in distilled water dissolved with detergent and washed with ultrasonic waves. At this time, the detergent used Fischer Co. products, and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, using nitrogen plasma, after the above-mentioned substrate was cleaned for 5 minutes, the substrate was transported to a vacuum deposition machine. On the ITO transparent electrode prepared in this way, the following HAT-CN compound was thermally vacuum deposited with a thickness of 5nm to form a hole injection layer. Next, HTL-1 was thermally vacuum deposited with a thickness of 100nm, and then HTL-2 was thermally vacuum deposited with a thickness of 10nm to form a hole transport layer. Next, the compound 1 (main body) synthesized in the above synthesis example and the following compound BD (dopant) (main compound weight ratio: dopant compound weight ratio = 95: 5) are vacuum-deposited at the same time to form a first light-emitting layer with a thickness of 85nm. Next, the following compound BH (main body) and the following compound BD (dopant) (main compound weight ratio: dopant compound weight ratio = 95: 5) are vacuum-deposited at the same time to form a second light-emitting layer with a thickness of 85nm. Next, the following compound ETL is vacuum-deposited at a thickness of 20nm to form an electron transport layer. Next, LiF is vacuum-deposited at a thickness of 0.5nm to form an electron injection layer. Next, aluminum is evaporated at a thickness of 100nm to form a cathode, thereby manufacturing an organic light-emitting device.

[0502] The structures of the compounds used in the Examples are shown below.

[0503]

[0504] Examples 2 to 15 and Comparative Examples 1 to 4.

[0505] In the above-mentioned Example 1, as the host of the first light-emitting layer, the compounds described in the following Table 1 were used instead of Compound 1, and an organic light-emitting device was prepared by the same method as in Example 1. At this time, the compounds represented by Chemical Formula 1 of the present invention in the following structures (Compounds 2 to 15) were prepared by the same process as in the above-mentioned Synthesis Examples 2 to 15.

[0506] The structures of the compounds used in Examples and Comparative Examples are shown below.

[0507]

[0508] In the organic light emitting devices manufactured in the above Examples 1 to 15 and Comparative Examples 1 to 4, at 10 mA / cm 2 The driving voltage (Voc) and luminous efficiency (cd / A) were measured at a current density of 20 mA / cm 2 The time (LT) until the luminance reaches 95% of the initial luminance was measured at a current density of 1.5 %. The results are shown in Table 1 below.

[0509]

Table 1

[0510]

[0511] Examples 1 to 15 using the compound represented by Chemical Formula 1 of the present invention all showed low voltage and high efficiency characteristics compared with Comparative Examples 1 to 4. In addition, Examples 14 and 15 using deuterium-substituted compounds showed further improved lifespans when compared with Examples 1 and 4, respectively.

[0512] Comparative Example 1 containing anthracene showed high driving voltage and low efficiency compared with Examples 1 to 15. In the present invention, Comparative Example 2 using compounds with different binding positions of Chemical Formula 1 and Chemical Formula 2 also showed high driving voltage and low efficiency compared with Examples 1 to 15. Comparative Examples 3 and 4 that did not contain Chemical Formula 2 of the present invention but contained dibenzofuranyl showed particularly high driving voltage characteristics compared with Examples 1 to 15.

[0513] The preferred embodiments (main body) of the present invention are described above, but the present invention is not limited thereto and can be implemented in various forms within the scope of the claims and the detailed description of the invention, which also belongs to the scope of the present invention.

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, One to four of R1 to R10 are combined with the following chemical formula 2, The remaining R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, [Chemical formula 2] In the chemical formula 2, X is O or S, L1 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted heteroarylene group, Any one of R11 to R14 is a moiety that binds to L1, The remaining R11 to R14 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, R15 to R17 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, l1 is an integer from 1 to 4. When l1 is 2 or more, two or more L1s are the same or different from each other. n is an integer of 1 or 2. When n is 2, the structures in the brackets are the same or different from each other. * is a part combined with the chemical formula 1.

2. The compound according to claim 1, wherein The chemical formula 2 is any one of the following chemical formulas 2-1 to 2-4: [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3] [Chemical formula 2-4] In the chemical formulas 2-1 to 2-4, *, X, L1 and l1 are the same as those defined in the chemical formula 2, R11 to R17 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

3. The compound according to claim 1, wherein One or two of the R1 to R10 are combined with the chemical formula 2, and the remaining R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

4. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-3: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] In the chemical formulas 1-1 to 1-3, R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, is a portion combined with the chemical formula 2.

5. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-11 to 1-15: [Chemical formula 1-11] [Chemical formula 1-12] [Chemical formula 1-13] [Chemical formula 1-14] [Chemical formula 1-15] In the chemical formulas 1-11 to 1-15, R2 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, is a portion combined with the chemical formula 2.

6. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-21 to 1-27: [Chemical formula 1-21] [Chemical formula 1-22] [Chemical formula 1-23] [Chemical formula 1-24] [Chemical formula 1-25] [Chemical formula 1-26] [Chemical formula 1-27] In the chemical formulas 1-21 to 1-27, R1 and R3 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, is a portion combined with the chemical formula 2.

7. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-31 to 1-33: [Chemical formula 1-31] [Chemical formula 1-32] [Chemical formula 1-33] In the chemical formulas 1-31 to 1-33, R1, R2, and R4 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, is a portion combined with the chemical formula 2.

8. The compound according to claim 1, wherein One to four of the R1 to R10 are combined with the chemical formula 2, and the remaining R1 to R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

9. The compound according to claim 1, wherein Any one of R11 to R14 is a portion that binds to L1, and the remaining R11 to R14 are the same as or different from each other, and are independently hydrogen or deuterium.

10. The compound according to claim 1, wherein The R15 to R17 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

11. The compound according to claim 1, wherein The compound is any one of the following structures:

12. An organic light emitting device, comprising: The first electrode, a second electrode, and One or more organic layers are provided between the first electrode and the second electrode, One or more of the organic layers contains the compound according to any one of claims 1 to 11.

13. The organic light emitting device according to claim 12, wherein: The organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as a host of the light-emitting layer.

14. The organic light emitting device according to claim 13, wherein: The light-emitting layer includes a dopant, and the dopant includes a fluorescent dopant.

15. The organic light emitting device according to claim 14, wherein: The fluorescent dopant includes at least one selected from pyrene compounds and non-pyrene compounds.

16. The organic light emitting device according to claim 15, wherein: The non-pyrene-based compounds include boron-based compounds.

17. An organic light emitting device, comprising: The first electrode, The second electrode, 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, The first light-emitting layer comprises the compound according to any one of claims 1 to 11, The second light-emitting layer comprises a compound of the following chemical formula 5: [Chemical formula 5] In the chemical formula 5, L20 and L21 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group, Ar20 and Ar21 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, R301 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, r301 is an integer of 1 to 8. When r301 is 2 or more, two or more R301s are the same as or different from each other.

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