Organic light emitting device

Abstract

The present specification provides an organic light-emitting device having low driving voltage, high efficiency, and long lifespan, the organic light-emitting device including: a first electrode; a second electrode disposed opposite the first electrode; and a first organic material layer and a second organic material layer disposed between the first electrode and the second electrode, in which the first organic material layer and the second organic material layer are disposed adjacent to each other, the first organic material layer including a compound represented by Chemical Formula 1 in which dibenzofuran is bonded to anthracene; and the second organic material layer contains a compound represented by chemical formula 2 in which an N-containing heterocyclic group and spirofluorene xanthene are bonded.

Description

[0001] This application is a divisional application of an application with an application date of July 25, 2019, application number 201980033886.0, and invention name “Organic Light-Emitting Device” (PCT / KR2019 / 009259, entering the national phase date of November 19, 2020). Technical Field

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0086643 filed in the Korean Intellectual Property Office on July 25, 2018, the entire contents of which are incorporated herein by reference.

[0003] The present disclosure relates to organic light emitting devices. Background Art

[0004] Recently, interest and demand in the display field have grown rapidly, and among display devices, organic light emitting devices have attracted attention due to their potential for low power consumption and thin devices.

[0005] Therefore, the development of organic light-emitting devices with excellent efficiency and long life characteristics has been continued. In particular, blue light-emitting devices have a problem of significantly poor efficiency and life compared with green phosphorescent devices and red phosphorescent devices, and research on methods for significantly improving the efficiency and life of blue light-emitting devices has been continued.

[0006] [Prior art document] (Patent document 1) Korean Patent Application Publication No. 10-2008-0095244 Summary of the invention

[0007] Technical issues

[0008] The present disclosure describes organic light emitting devices having low driving voltage, high efficiency, and long lifetime characteristics.

[0009] Technical Solution

[0010] One embodiment of the present disclosure provides an organic light-emitting device, comprising: a first electrode; a second electrode arranged opposite to the first electrode; and a first organic material layer and a second organic material layer arranged between the first electrode and the second electrode, wherein the first organic material layer contains a compound represented by the following Chemical Formula 1, and the second organic material layer contains a compound represented by the following Chemical Formula 2.

[0011] [Chemical formula 1]

[0012]

[0013] In Chemical Formula 1,

[0014] L1 and L2 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group,

[0015] R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted haloalkyl group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or are bonded to an adjacent group to form a substituted or unsubstituted ring,

[0016] n1 is an integer of 0 to 7, and when n1 is 2 or more, two or more R1 are the same as or different from each other,

[0017] n2 is an integer from 0 to 9, and when n2 is 2 or more, two or more -L2-R2 are the same as or different from each other, and

[0018] n3 is 1 or 2, and when n3 is 2, the substituents in the two brackets are the same as or different from each other, and 1≤n2+n3≤10,

[0019] [Chemical formula 2]

[0020]

[0021] In chemical formula 2,

[0022] At least one of X1 to X3 is N, and the rest are CR,

[0023] R and Ar1 to Ar3 are the same as or different from each other, and are each independently hydrogen; deuterium; cyano; nitrile; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted haloalkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group, or bond with an adjacent group to form a substituted or unsubstituted ring, and at least one of Ar1 to Ar3 is represented by the following Chemical Formula 3,

[0024] L11 to L13 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, and

[0025] m1 to m3 are each an integer of 0 to 3, and when m1 to m3 are each 2 or more, two or more substituents in brackets are the same as or different from each other,

[0026] [Chemical formula 3]

[0027]

[0028] In chemical formula 3,

[0029] Any one of R11 to R26 is connected to any one of L11 to L13, and the rest are hydrogen; deuterium; cyano; nitrile; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0030] Beneficial Effects

[0031] Since the organic light emitting device of the present disclosure includes the compound represented by Chemical Formula 1 in the first organic material layer and the compound represented by Chemical Formula 2 in the second organic material layer, a device having low driving voltage, excellent efficiency and long lifespan may be obtained. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] Figures 1 to 4 An example of an organic light emitting device of the present disclosure is shown.

[0033] [reference numerals]

[0034] 0: Base

[0035] 1: Cathode

[0036] 2: Electron transport layer

[0037] 3: Hole transport layer

[0038] 4: Anode

[0039] 5: Organic material layer

[0040] 6: Organic material layer

[0041] 7: Hole blocking layer or electron control layer

[0042] 11: Luminous layer 1

[0043] 12: Luminous layer 2

[0044] 13: Luminous layer 3

[0045] 101: Luminous Layer

[0046] 102: Hole injection layer

[0047] 103: Hole transport layer

[0048] 104: Hole blocking layer or electron control layer

[0049] 105: Electron injection and transport layer DETAILED DESCRIPTION

[0050] Hereinafter, the present specification will be described in more detail.

[0051] The organic light emitting device of the present disclosure includes a first electrode; a second electrode disposed opposite to the first electrode; and a first organic material layer and a second organic material layer disposed between the first electrode and the second electrode, wherein the first organic material layer includes a compound represented by the following Chemical Formula 1, and the second organic material layer includes a compound represented by the following Chemical Formula 2. Since the first organic material layer and the second organic material layer simultaneously include a dibenzofuran-based compound or a xanthene-based compound each containing an oxygen (O) atom, a device having excellent characteristics can be obtained by improving the mobility of electrons.

[0052] In particular, according to one embodiment of the present disclosure, the first organic material layer and the second organic material layer may be disposed adjacent to each other. Here, since the first organic material layer and the second organic material layer simultaneously contain a dibenzofuran-based compound or a xanthene-based compound each containing an oxygen (O) atom, when the organic material layer film is formed, the molecular arrangement occurs favorably by the influence of the substituent containing the oxygen (O) atom, which hardens the film quality, thereby effectively improving the device life. In addition, the electron mobility is improved by reducing the barrier between the interfaces, and a voltage reduction, an efficiency improvement, and an increase in life are obtained in the device.

[0053] [Chemical formula 1]

[0054]

[0055] In Chemical Formula 1,

[0056] L1 and L2 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group,

[0057] R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted haloalkyl group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or are bonded to an adjacent group to form a substituted or unsubstituted ring,

[0058] n1 is an integer of 0 to 7, and when n1 is 2 or more, two or more R1 are the same as or different from each other,

[0059] n2 is an integer from 0 to 9, and when n2 is 2 or more, two or more -L2-R2 are the same as or different from each other, and

[0060] n3 is 1 or 2, and when n3 is 2, the substituents in the two brackets are the same as or different from each other, and 1≤n2+n3≤10,

[0061] [Chemical formula 2]

[0062]

[0063] In chemical formula 2,

[0064] At least one of X1 to X3 is N, and the rest are CR,

[0065] R and Ar1 to Ar3 are the same as or different from each other, and are each independently hydrogen; deuterium; cyano; nitrile; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted haloalkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group, or bond with an adjacent group to form a substituted or unsubstituted ring, and at least one of Ar1 to Ar3 is represented by the following Chemical Formula 3,

[0066] L11 to L13 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, and

[0067] m1 to m3 are each an integer of 0 to 3, and when m1 to m3 are each 2 or more, two or more substituents in brackets are the same as or different from each other,

[0068] [Chemical formula 3]

[0069]

[0070] In chemical formula 3,

[0071] Any one of R11 to R26 is connected to any one of L11 to L13, and the rest are hydrogen; deuterium; cyano; nitrile; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0072] In the present disclosure, that the first organic material layer and the second organic material layer are disposed 'adjacent' to each other means that one surface of the first organic material layer and one surface of the second organic material layer are formed to be in physical contact with each other.

[0073] In the present disclosure, unless specifically described otherwise, a description that a certain component “includes” certain constituent elements means that other constituent elements can be further included, and does not exclude other constituent elements.

[0074] In the present disclosure, description that a certain component is placed “on” another component includes not only a case where one component is adjacent to another component but also a case where another component exists between the two components.

[0075] Examples of the substituent in the present disclosure will be described below, however, the substituent is not limited thereto.

[0076] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position of substitution is not limited as long as it is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substituents are substituted, the two or more substituents can be the same or different from each other.

[0077] The term "substituted or unsubstituted" in the present disclosure means substituted with one, two or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group (-CN), a nitro group, a silyl group, a boron group, an alkyl group, an alkenyl group, a haloalkyl group, a haloalkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent in which two or more of the substituents shown above are linked, or having no substituent.

[0078] Examples of the substituent will be described below, however, the substituent is not limited thereto.

[0079] In the present disclosure, examples of the halogen group may include fluorine (—F), chlorine (—Cl), bromine (—Br), or iodine (—I).

[0080] In the present disclosure, the alkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 40. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, and the like, but are not limited thereto.

[0081] In the present disclosure, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0082] In the present disclosure, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and the aryl group may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. When the aryl group is a monocyclic aryl group, examples thereof may include phenyl, biphenyl, terphenyl, quaterphenyl, etc., but are not limited thereto. Examples of polycyclic aryl groups may include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, base, phenylene, fluorenyl, triphenylene, phenalenyl, etc., but not limited thereto.

[0083] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro ring structure.

[0084] When the fluorenyl group is substituted, it may include a spirofluorenyl group (e.g. ) and substituted fluorenyl (e.g. (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl)), however, the structure is not limited thereto.

[0085] In the present disclosure, the heterocyclic group is a cyclic group containing one or more of N, O, S, P and Si as a heteroatom, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group may include a pyridyl group, a furyl group, a thienyl group, a dibenzofuranyl group, a carbazolyl group, a dibenzothienyl group, a naphthobenzofuranyl group, a naphthobenzothienyl group, a phenanthroline group, a thiophene ... Thiol, dibenzothioyl, indenocarbazolyl, etc., but not limited thereto.

[0086] In the present disclosure, the description provided above regarding heterocyclyl groups can be applied to heteroaryl groups, except that the heteroaryl groups are aromatic.

[0087] In the present disclosure, the "ring" in a substituted or unsubstituted ring formed by bonding to each other means a hydrocarbon ring; or a heterocyclic ring.

[0088] The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of cycloalkyl or aryl groups, except that the hydrocarbon ring is divalent.

[0089] In the present disclosure, the description about the aryl group may be applied to the aromatic hydrocarbon ring, except that the aromatic hydrocarbon ring is divalent.

[0090] In the present disclosure, the description about the heterocyclic group can be applied to the heterocycle, except that the heterocycle is divalent.

[0091] In the present disclosure, the description about the heteroaryl group can be applied to the aromatic heterocycle, except that the aromatic heterocycle is divalent.

[0092] In the present disclosure, the description about the aryl group may be applied to the arylene group, except that the arylene group is divalent.

[0093] In the present disclosure, the description about the heteroaryl group may be applied to the heteroarylene group, except that the heteroarylene group is divalent.

[0094] According to one embodiment of the present disclosure, the first organic material layer is a light emitting layer.

[0095] According to one embodiment of the present disclosure, the first organic material layer is a light emitting layer, and the light emitting layer includes one or more types of compounds represented by Chemical Formula 1. The light emitting layer including one or more types of compounds represented by Chemical Formula 1 further includes a fluorescent dopant.

[0096] In another embodiment, the first organic material layer is a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1 as a host of the light emitting layer.

[0097] According to another embodiment, the first organic material layer is a light-emitting layer, and the light-emitting layer includes a compound represented by Chemical Formula 1 as a main body of the light-emitting layer, and may further include one or more types of compounds represented by the following Chemical Formula A and compounds represented by the following Chemical Formula B as main bodies. Here, the weight ratio of the compound represented by Chemical Formula 1 to the compound represented by the following Chemical Formula A and the compound represented by the following Chemical Formula B in the light-emitting layer (the weight of the compound represented by Chemical Formula 1: the weight of the compound represented by Chemical Formula A and the compound represented by Chemical Formula B) may be 1:9 to 9:1.

[0098] [Chemical formula A]

[0099]

[0100] In chemical formula A,

[0101] L31 and L32 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms and containing any one or more heteroatoms selected from N, O and S,

[0102] Ar31 and Ar32 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms and containing any one or more heteroatoms selected from N, O and S,

[0103] [Chemical formula B]

[0104]

[0105] In chemical formula B,

[0106] L33, L34 and L35 are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms and containing any one or more heteroatoms selected from N, O and S, and

[0107] Ar33, Ar34 and Ar35 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms and containing any one or more heteroatoms selected from N, O and S.

[0108] In one embodiment of the present disclosure, the compound represented by Chemical Formula A is any one of the following structures.

[0109]

[0110]

[0111] In another embodiment, the first organic material layer is a light-emitting layer, and the light-emitting layer includes a compound represented by Chemical Formula 1 as a host of the light-emitting layer, and may further include a dopant. The dopant may be a fluorescent dopant or a phosphorescent dopant, and is preferably a fluorescent dopant. Here, based on 100 parts by weight of the host, the dopant may be included in the light-emitting layer in an amount of 0.1 to 50 parts by weight, and preferably in an amount of 1 to 30 parts by weight.

[0112] In the present disclosure, any one of the following structures may be used as a fluorescent dopant, however, the fluorescent dopant is not limited thereto.

[0113]

[0114] In the present disclosure, an Ir complex may be used as a phosphorescent dopant, and for example, any one of the following structures may be used, however, the phosphorescent dopant is not limited thereto.

[0115]

[0116] The first organic material layer includes a compound represented by Chemical Formula 1.

[0117] According to one embodiment of the present disclosure, n3 is 1 or 2, and when n3 is 2, the substituents in the two brackets are the same as or different from each other, and 1≤n2+n3≤10.

[0118] According to one embodiment of the present disclosure, n2 is an integer from 0 to 2, and when n2 is 2, two -L2-R2 are the same as or different from each other.

[0119] According to one embodiment of the present disclosure, n1 is an integer from 0 to 2, and when n1 is 2, two R1s are the same as or different from each other.

[0120] In one embodiment of the present disclosure, R1 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms.

[0121] According to another embodiment, R1 is hydrogen or deuterium, or when n1 is 2, two R1s are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0122] In another embodiment, R1 is hydrogen or deuterium, or when n1 is 2, two R1 are bonded to each other to form a substituted or unsubstituted benzene ring and form naphthobenzofuran.

[0123] According to another embodiment, R1 is hydrogen or deuterium, or when n1 is 2, two R1 are bonded to each other to form a benzene ring, and naphthobenzofuran is formed.

[0124] According to one embodiment of the present disclosure, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0125] According to another embodiment, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0126] In another embodiment, L1 is a direct bond.

[0127] According to one embodiment of the present disclosure, L2 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0128] According to another embodiment, L2 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0129] In another embodiment, L2 is a direct bond; substituted or unsubstituted phenylene; substituted or unsubstituted biphenylene; substituted or unsubstituted naphthylene; or substituted or unsubstituted phenanthrenylene.

[0130] According to another embodiment, L2 is a direct bond; phenylene; biphenylene; naphthylene; or phenanthrylene.

[0131] According to one embodiment of the present disclosure, R1 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0132] According to another embodiment, R1 is hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclyl group having 2 to 30 carbon atoms and comprising one or more of O, S and N as heteroatoms.

[0133] In another embodiment, R1 is hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthrenyl; or substituted or unsubstituted dibenzofuranyl.

[0134] According to another embodiment, R1 is hydrogen; deuterium; phenyl; biphenyl; naphthyl; phenanthrenyl; or dibenzofuranyl.

[0135] In one embodiment of the present disclosure, the compound represented by Chemical Formula 1 is represented by any one of the following structures.

[0136]

[0137]

[0138] According to one embodiment of the present disclosure, the second organic material layer is a hole blocking layer or an electron control layer.

[0139] According to another embodiment, the first organic material layer is a light-emitting layer, the second organic material layer is a hole blocking layer or an electron control layer, and the light-emitting layer and the hole blocking layer or the electron control layer are disposed adjacent to each other.

[0140] In one embodiment of the present disclosure, the second organic material layer is a hole blocking layer or an electron control layer, and the hole blocking layer or the electron control layer includes a compound represented by Chemical Formula 2.

[0141] The second organic material layer includes a compound represented by Chemical Formula 2.

[0142] According to one embodiment of the present disclosure, at least one of X1 to X3 is N, and the rest are CR.

[0143] According to one embodiment of the present disclosure, R and Ar1 to Ar3 are the same as or different from each other and are each independently hydrogen; deuterium; cyano; nitrile; substituted or unsubstituted trialkylsilyl having 1 to 20 carbon atoms; substituted or unsubstituted triarylsilyl having 6 to 30 carbon atoms; substituted or unsubstituted alkyl having 1 to 20 carbon atoms; substituted or unsubstituted haloalkyl having 1 to 20 carbon atoms; substituted or unsubstituted alkyl having 3 to 4 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and containing one or more of O, S, N and Si as a heteroatom, or is bonded with an adjacent group to form a substituted or unsubstituted ring having 3 to 30 carbon atoms, and at least one of Ar1 to Ar3 is represented by the following Chemical Formula 3.

[0144] According to another embodiment, R and Ar1 to Ar3 are the same as or different from each other and are each independently hydrogen; deuterium; cyano; nitrile; substituted or unsubstituted trialkylsilyl having 1 to 20 carbon atoms; substituted or unsubstituted triarylsilyl having 6 to 30 carbon atoms; substituted or unsubstituted alkyl having 1 to 20 carbon atoms; substituted or unsubstituted haloalkyl having 1 to 20 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms; substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and containing one or more of O, S, N and Si as a heteroatom, or Ar1 and R are bonded to each other to form a substituted or unsubstituted ring having 3 to 30 carbon atoms, Ar2 and R are bonded to each other to form a substituted or unsubstituted ring having 3 to 30 carbon atoms, and at least one of Ar1 to Ar3 is represented by the following Chemical Formula 3.

[0145] In another embodiment, R and Ar1 to Ar3 are the same as or different from each other and are each independently hydrogen; deuterium; cyano; a substituted or unsubstituted trialkylsilyl group having 1 to 20 carbon atoms; a substituted or unsubstituted triarylsilyl group having 6 to 30 carbon atoms; a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and containing one or more of O, S, N and Si as a heteroatom, or Ar1 and R, or Ar2 and R are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, and at least one of Ar1 to Ar3 is represented by the following Chemical Formula 3.

[0146] According to another embodiment, R and Ar1 to Ar3 are the same as or different from each other and are each independently hydrogen; deuterium; cyano; substituted or unsubstituted trifluoromethyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted carbazolyl; substituted or unsubstituted triphenylene; substituted or unsubstituted dibenzothiophenyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted phenanthroline; Thiol; substituted or unsubstituted phenanthrenyl; substituted or unsubstituted phenalenyl; substituted or unsubstituted benzocarbazolyl; substituted or unsubstituted pyridyl; substituted or unsubstituted indenocarbazolyl; substituted or unsubstituted trimethylsilyl; substituted or unsubstituted triphenylsilyl; or substituted or unsubstituted dibenzothioyl, or selected from the following structures, and the following structures may be substituted or unsubstituted.

[0147]

[0148] In the structures, * means the bonding position.

[0149] R and Ar1 to Ar3 may be unsubstituted or substituted with substituents linked to one or more of the following: hydrogen; deuterium; cyano; trifluoromethyl; a trialkylsilyl group having 1 to 20 carbon atoms; a triarylsilyl group having 6 to 30 carbon atoms; an alkyl group having 1 to 20 carbon atoms; an aryl group having 6 to 30 carbon atoms; and a heterocyclic group having 2 to 30 carbon atoms and containing one or more of O, S, N and Si as heteroatoms.

[0150] R and Ar1 to Ar3 may be unsubstituted or substituted with substituents connected by one or more of the following: hydrogen; deuterium; cyano; trifluoromethyl; a trialkylsilyl group having 1 to 10 carbon atoms; a triarylsilyl group having 6 to 20 carbon atoms; an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 20 carbon atoms; and a heterocyclic group having 2 to 20 carbon atoms and containing one or more of O, S, N and Si as heteroatoms.

[0151] R and Ar1 to Ar3 can be unsubstituted or substituted with one or more of the following substituents connected: hydrogen; deuterium; cyano; trifluoromethyl; trimethylsilyl; triphenylsilyl; methyl; phenyl; biphenyl; naphthyl; dimethylfluorenyl; diphenylfluorenyl; dibenzofuranyl; dibenzothiophenyl; and carbazolyl.

[0152] According to another embodiment, R and Ar1 to Ar3 are the same or different from each other and are each independently hydrogen; deuterium; cyano; trifluoromethyl; phenyl; biphenyl; unsubstituted or pyridyl-substituted terphenyl; naphthyl; unsubstituted or methyl- or phenyl-substituted carbazolyl; triphenylene; unsubstituted or methyl-substituted dibenzothiophenyl; dibenzofuranyl; phenanthroline; Thianyl; phenanthrenyl; benzocarbazolyl; pyridyl; unsubstituted or methyl-substituted N-phenylindenocarbazolyl; trimethylsilyl; triphenylsilyl; or methyl-substituted dibenzothiazolyl, or selected from the following structures.

[0153]

[0154] In the structures, * means the bonding position.

[0155] In one embodiment of the present disclosure, Ar1 and R, or Ar2 and R, are bonded to each other to form a substituted or unsubstituted benzene.

[0156] According to another embodiment, Ar1 and R, or Ar2 and R, are bonded to each other to form benzene which is unsubstituted or substituted with a benzocarbazolyl group.

[0157] According to one embodiment of the present disclosure, L11 to L13 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

[0158] In another embodiment, L11 to L13 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms and containing one or more of O, S, N and Si as a heteroatom.

[0159] According to one embodiment of the present disclosure, L11 to L13 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; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted divalent dibenzothiophenyl group; a substituted or unsubstituted divalent dibenzofuranyl group; a substituted or unsubstituted divalent carbazolyl group; a substituted or unsubstituted divalent benzocarbazolyl group; a substituted or unsubstituted divalent indenocarbazolyl group; a substituted or unsubstituted divalent dibenzosilyl group; a substituted or unsubstituted divalent phenoxy group; thiol; a substituted or unsubstituted divalent pyridyl; a substituted or unsubstituted divalent thienyl; or a substituted or unsubstituted divalent furyl, or is selected from the following structures, and the following structures may be substituted or unsubstituted.

[0160]

[0161] In the structures, * means the bonding position.

[0162] According to another embodiment, L11 to L13 are the same as or different from each other and are each independently a direct bond; a phenylene group which is unsubstituted or substituted with a methyl group, a phenyl group or a dibenzothienyl group; a biphenylene group; a naphthyl group; a dimethylfluorenyl group; a divalent dibenzothienyl group; a divalent dibenzofuranyl group; a divalent carbazolyl group which is unsubstituted or substituted with a phenyl group; a divalent benzocarbazolyl group which is unsubstituted or substituted with a phenyl group or a dimethylbiphenyl group; a divalent indenocarbazolyl group which is substituted with a methyl group; a divalent dimethyldibenzothioyl group; a divalent phen Thiol; divalent pyridyl; divalent thienyl; or divalent furyl, or the following structure.

[0163]

[0164] In the structures, * means the bonding position.

[0165] According to one embodiment of the present disclosure, one or both of Ar1 to Ar3 are represented by the following Chemical Formula 3.

[0166] [Chemical formula 3]

[0167]

[0168] In chemical formula 3,

[0169] Any one of R11 to R26 is connected to any one of L11 to L13, and the rest are hydrogen; deuterium; cyano; nitrile; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0170] In one embodiment of the present disclosure, any one of R11 to R26 is connected to any one of L11 to L13, and the rest are hydrogen; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0171] In another embodiment, any one of R11 to R26 is connected to any one of L11 to L13, and the rest are hydrogen; substituted or unsubstituted methyl; substituted or unsubstituted butyl; substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; or substituted or unsubstituted fluorenyl, or bonded to an adjacent group to form a substituted or unsubstituted benzene ring.

[0172] According to one embodiment of the present disclosure, any one of R11 to R26 is connected to any one of L11 to L13, and the rest are hydrogen; methyl; tert-butyl; n-butyl; unsubstituted or methyl-substituted phenyl; naphthyl; or dimethylfluorenyl, or bonded to an adjacent group to form a benzene ring.

[0173] According to one embodiment of the present specification, any one of R11 to R18 is connected to any one of L11 to L13, and the rest are hydrogen; methyl; tert-butyl; n-butyl; unsubstituted or methyl-substituted phenyl; naphthyl; or dimethylfluorenyl, or bonded to an adjacent group to form a benzene ring.

[0174] According to one embodiment of the present specification, any one of R19 to R26 is connected to any one of L11 to L13, and the rest are hydrogen; methyl; tert-butyl; n-butyl; unsubstituted or methyl-substituted phenyl; naphthyl; or dimethylfluorenyl, or bonded to an adjacent group to form a benzene ring.

[0175] According to one embodiment of the present specification, Chemical Formula 2 is represented by any one of the following Chemical Formulas 201 to 203.

[0176] [Chemical formula 201]

[0177]

[0178] [Chemical formula 202]

[0179]

[0180] [Chemical formula 203]

[0181]

[0182] In Chemical Formulas 201 to 203, X1 to X3, Ar2 to Ar3, L11 to L13, m1 to m3 and R11 to R26 have the same definitions as in Chemical Formulas 2 and 3, R31 and R32 have the same definitions as R11 to R26 in Chemical Formula 3, and r31 and r32 are integers of 1 to 7.

[0183] In one embodiment of the present specification, Chemical Formula 2 is represented by any one of the following structures.

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212] According to one embodiment of the present disclosure, the first organic material layer is a light-emitting layer, the light-emitting layer includes the compound represented by Chemical Formula 1 above, and the maximum light-emitting peak of the light-emitting layer is 400 nm to 500 nm.

[0213] According to one embodiment of the present disclosure, the organic light-emitting device further comprises one or more light-emitting layers. The one or more light-emitting layers may each contain the above-mentioned fluorescent dopant or phosphorescent dopant.

[0214] According to another embodiment, the organic light-emitting device further includes one or more light-emitting layers having a maximum light-emitting peak in a wavelength range different from the wavelength range of the maximum light-emitting peak of the light-emitting layer containing one or more types of compounds represented by Chemical Formula 1. Here, the maximum light-emitting peak of the light-emitting layer containing one or more types of compounds represented by Chemical Formula 1 is 400nm to 500nm, and the one or more light-emitting layers having a maximum light-emitting peak in a wavelength range different from the wavelength range of the maximum light-emitting peak of the light-emitting layer containing one or more types of compounds represented by Chemical Formula 1 may have a maximum light-emitting peak appearing at 510nm to 580nm or 610nm to 680nm. The one or more light-emitting layers having a maximum light-emitting peak in a wavelength range different from the wavelength range of the maximum light-emitting peak of the light-emitting layer containing one or more types of compounds represented by Chemical Formula 1 include a phosphorescent dopant.

[0215] According to one embodiment of the present disclosure, the first organic material layer of the organic light-emitting device is a light-emitting layer, the light-emitting layer includes the compound represented by Chemical Formula 1 and further includes a fluorescent dopant, the organic light-emitting device further includes one or more light-emitting layers, and the one or more light-emitting layers include a phosphorescent dopant.

[0216] In another embodiment, the organic light emitting device includes one or more light emitting layers having a maximum light emitting peak in the same wavelength range as the wavelength range of the maximum light emitting peak of the light emitting layer including one or more types of compounds represented by Chemical Formula 1. Here, the maximum light emitting peak of the light emitting layer is 400nm to 500nm.

[0217] According to one embodiment of the present disclosure, the first organic material layer of the organic light-emitting device is a light-emitting layer, the light-emitting layer includes the compound represented by Chemical Formula 1 and further includes a fluorescent dopant, the organic light-emitting device further includes one or more light-emitting layers, and the one or more light-emitting layers include a fluorescent dopant.

[0218] In addition, when the organic light emitting device of the present disclosure includes two or more light emitting layers, the two or more light emitting layers may be sequentially laminated in a vertical direction, or may be laminated side by side in a horizontal direction.

[0219] Figures 1 to 4 Each shows a laminated structure of an organic light-emitting device of the present disclosure including two or more light-emitting layers.

[0220] Figure 1 An organic light-emitting device is shown in which a substrate 0, a cathode 1, an electron transport layer 2, a hole blocking layer or electron control layer 7, a light-emitting layer 101, a hole transport layer 3 and an anode 4 are sequentially layered, and as the light-emitting layer 101, the light-emitting layer 1 11 and the light-emitting layer 2 12 are layered side by side in a horizontal direction.

[0221] Figure 2 An organic light-emitting device is shown in which a substrate 0, a cathode 1, an electron transport layer 2, a hole blocking layer or electron control layer 7, a light-emitting layer 1 11, an organic material layer 5, a light-emitting layer 2 12, a hole transport layer 3 and an anode 4 are sequentially stacked in a vertical direction.

[0222] Figure 3 An organic light-emitting device is shown in which a substrate 0, a cathode 1, an electron transport layer 2, a hole blocking layer or electron control layer 7, a light-emitting layer 1 11, an organic material layer 5, a light-emitting layer 2 12, an organic material layer 6, a light-emitting layer 3 13, a hole transport layer 3 and an anode 4 are sequentially stacked in a vertical direction.

[0223] Figure 4An organic light-emitting device is shown in which a substrate 0, an anode 4, a hole injection layer 102, a hole transport layer 103, a light-emitting layer 101, a hole blocking layer or electron control layer 104, an electron injection and transport layer 105, and a cathode 1 are sequentially stacked in a vertical direction.

[0224] Compounds having various energy band gaps can be synthesized in the present disclosure by introducing various substituents into the core structures of Chemical Formula 1 and Chemical Formula 2. In addition, the HOMO and LUMO energy levels of the compounds can also be controlled in the present disclosure by introducing various substituents into the core structures having the above structures.

[0225] The organic light-emitting device of the present disclosure can be manufactured using common organic light-emitting device manufacturing methods and materials, except that the compound represented by Chemical Formula 1 is used to form the first organic material layer, and the compound represented by Chemical Formula 2 is used to form the second organic material layer.

[0226] When manufacturing an organic light-emitting device in which a first organic material layer including a compound represented by Chemical Formula 1 and a second organic material layer including a compound represented by Chemical Formula 2 are formed, a solution coating method as well as a vacuum deposition method may be used when forming the organic material layer. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0227] The organic light-emitting device of the present disclosure may be formed with one or more of the following organic material layers: a hole transport layer, a hole injection layer, an electron blocking layer, a hole control layer, a layer for simultaneous hole transport and hole injection, a light-emitting layer, an electron injection layer, an electron transport layer, a hole blocking layer, an electron control layer, and a layer for simultaneous electron transport and electron injection, and the first organic material layer is a light-emitting layer, and the second organic material layer is a hole blocking layer and / or an electron control layer. However, the structure of the organic light-emitting device of the present specification is not limited thereto, and may include a greater number of organic material layers.

[0228] In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

[0229] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0230] The organic light-emitting device according to the present disclosure can be manufactured by forming an anode on a substrate by depositing a metal, a conductive metal oxide, or an alloy thereof using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic material layer including one or more layers formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron transport layer, a layer for simultaneously performing hole transport and hole injection, a hole blocking layer, a layer for simultaneously performing electron transport and electron injection, and an electron injection layer on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to such a method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0231] The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer for simultaneous hole transport and hole injection, an electron blocking layer, a hole blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneous electron transport and electron injection, etc., but is not limited thereto, and may have a single-layer structure.

[0232] The anode is an electrode that injects holes, and as an anode material, a material having a large work function is generally preferred so that hole injection into the organic material layer is smooth. Specific examples of anode materials that can be used in the present disclosure include metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.

[0233] The cathode is an electrode that injects electrons, and as a cathode material, a material having a small work function is generally preferred so that electron injection into the organic material layer is smooth. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; and the like, but are not limited thereto. In addition, the cathode may be formed into one or two layers.

[0234] In the organic light emitting device of the present disclosure, the organic material layer may include an electron blocking layer, and as the electron blocking layer, a material known in the art may be used.

[0235] The hole injection layer is a layer that plays a role in smoothly injecting holes from the anode into the light-emitting layer, and the hole injection material is a material that can favorably receive holes from the anode at a low voltage. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on organic materials, anthraquinone, and polyaniline-based and polythiophene-based conductive polymers, etc., but are not limited thereto.

[0236] The hole transport layer can play a role in smoothly transporting holes. As a hole transport material, a material that can receive holes from the anode or the hole injection layer, move the holes to the light-emitting layer, and has a high hole mobility is suitable. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both conjugated parts and non-conjugated parts, etc., but are not limited thereto.

[0237] In the present disclosure, the light emitting layer may emit blue light, green light, or red light, may be formed of a phosphorescent material or a fluorescent material, and the light emitting layer includes a host and a dopant.

[0238] The host of the light-emitting layer may include a fused aromatic ring derivative, a heterocyclic compound, etc. Specifically, as a fused aromatic ring derivative, anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., may be included, and as a heterocyclic compound, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc. may be included, however, the host material is not limited thereto, and the compound represented by Chemical Formula 1 above may be used.

[0239] When the light-emitting layer emits red light, a phosphorescent material such as bis(1-phenylisoquinoline) iridium acetylacetonate (PIQIr(acac)), bis(1-phenylquinoline) iridium acetylacetonate (PQIr(acac)), tris(1-phenylquinoline) iridium (PQIr) or platinum octaethylporphyrin (PtOEP), or a fluorescent material such as tris(8-hydroxyquinoline) aluminum (Alq3) can be used as a light-emitting dopant, however, the light-emitting dopant is not limited thereto. When the light-emitting layer emits green light, a phosphorescent material such as fac tris(2-phenylpyridine) iridium (Ir(ppy)3) or a fluorescent material such as tris(8-hydroxyquinoline) aluminum (Alq3) can be used as a light-emitting dopant, however, the light-emitting dopant is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), a PFO-based polymer or a PPV-based polymer can be used as a light-emitting dopant, however, the light-emitting dopant is not limited thereto.

[0240] The electron transport layer can play a role in smoothly transporting electrons. As the electron transport material, a material that can advantageously receive electrons from the cathode, move the electrons to the light-emitting layer, and has high electron mobility is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes, etc., but are not limited thereto.

[0241] The electron injection layer can play a role in smoothly injecting electrons. As the electron injection material, a compound having electron transport ability, having an effect of injecting electrons from the cathode, having an excellent electron injection effect on the light-emitting layer or the light-emitting material, and preventing the excitons generated in the light-emitting layer from moving to the hole injection layer, and in addition, having an excellent thin film forming ability is preferred. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, Tetracarboxylic acid, fluorenyl methane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0242] The metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) chlorogallium, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0243] The hole blocking layer is a layer that blocks holes from reaching the cathode, and can be disposed between the electron transport layer and the light emitting layer, and can generally be formed under the same conditions as the hole injection layer. Specific examples thereof may include Oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., however, the above-mentioned compound represented by Chemical Formula 2 may be used.

[0244] The electron control layer is a layer that controls electron migration to the light emitting layer, and a material known in the art may be used, and the compound represented by Chemical Formula 2 described above may be used.

[0245] The hole control layer is a layer that controls the migration of holes to the light emitting layer, and a material known in the art can be used.

[0246] The organic light emitting device according to the present disclosure may be a top emission type, a bottom emission type, or a dual emission type according to the materials used.

[0247] Embodiments of the invention

[0248] Hereinafter, this specification will be described in detail with reference to embodiments. However, embodiments according to this specification can be modified into various other forms, and the scope of this application should not be interpreted as being limited to the embodiments described below. The embodiments of this application are provided to more fully describe this specification to those of ordinary skill in the art.

[0249] <Synthesis example>

[0250] The following compounds 2-1 to 2-7 were prepared referring to the methods described in Korean Patent Nos. 10-1593368 and 10-1755986.

[0251]

[0252] <Examples and Comparative Examples>

[0253] Example 1-1

[0254] It is coated with a thickness of A glass substrate (corning 7059 glass) with indium tin oxide (ITO) as a thin film was placed in distilled water dissolved with a detergent and ultrasonically cleaned. A product of Fischer Co. was used as a detergent, and distilled water filtered twice with a filter manufactured by Millipore Co. was used as distilled water. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the cleaning with distilled water was completed, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone and methanol solvents in this order and then dried.

[0255] On the transparent ITO electrode prepared as above, hexanitrile hexaazatriphenylene (HAT-CN) was deposited by thermal vacuum deposition. A hole injection layer is formed by vacuum depositing HT1 on the hole injection layer. After that, the host BH1 compound and the dopant BD1 compound (weight ratio of BH1:BD1=97.5:2.5) were vacuum deposited thereon. On the light-emitting layer, the compound 2-1 of Example 1-1 in Table 1 was deposited to The thickness of the hole blocking layer (electron control layer) is then vacuum deposited with compound ET1 and lithium quinoline (LiQ) in a weight ratio of 1:1 to form a layer with a thickness of On the electron injection and transport layer, lithium fluoride (LiF) and aluminum are sequentially deposited to a thickness of 100 Å and 200 Å, respectively. and to form a cathode, and thus, an organic light emitting device was manufactured.

[0256] During the above process, the deposition rate of the organic material is maintained at The deposition rates of lithium fluoride and aluminum at the cathode were kept at The vacuum during deposition was maintained at 2 × 10 -7 Up to 5×10 -6 Entrust.

[0257]

[0258] Examples 1-2 to 1-7

[0259] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compounds 2-2 to 2-7 were used instead of Compound 2-1 in Example 1-1.

[0260]

[0261] Examples 2-1 to 2-3

[0262] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compounds BH2 to BH4 were used instead of Compound BH1 in Example 1-1.

[0263]

[0264] Comparative Examples 1 to 8

[0265] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of the following Table 1 was used instead of Compound BH1 in Example 1-1, and the compound of the following Table 1 was used instead of Compound 2-1.

[0266]

[0267] When 10 mA / cm 2 When a current of 100 ℃ was applied, the voltage, efficiency and lifespan were measured, and the results are shown in the following Table 1. Meanwhile, LT98 means the time taken for the luminance to decrease from the initial luminance to 98%.

[0268] [Table 1]

[0269]

[0270] Examples 1-1 to 1-7 and 2-1 to 2-3 use the compound of Chemical Formula 1 of the present application in which dibenzofuran is bonded to anthracene as the host of the light-emitting layer, and use the compound represented by Chemical Formula 2 in which a heterocyclic group containing N is bonded to spirofluorene xanthene in the hole blocking layer. Meanwhile, Comparative Examples 1 to 8 use an anthracene compound in which only an aryl group is bonded thereto as the host of the light-emitting layer instead of the compound of Chemical Formula 1 of the present application, or use a compound in which a heterocyclic group containing N is bonded to diphenylfluorene as the material of the hole blocking layer instead of the compound of Chemical Formula 2 of the present application.

[0271] As shown in Table 1, Examples 1-1 to 1-7 and 2-1 to 2-3 have characteristics of low driving voltage, high efficiency, and long lifespan compared to when only one of the compounds represented by Chemical Formulas 1 and 2 is used.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; as well as a first organic material layer and a second organic material layer disposed between the first electrode and the second electrode, wherein the first organic material layer and the second organic material layer are arranged adjacent to each other, wherein the first organic material layer comprises a compound represented by the following Chemical Formula 1; and The second organic material layer includes a compound represented by the following Chemical Formula 2: [Chemical formula 1] In Chemical Formula 1, L1 and L2 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group; R1 and R2 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted haloalkyl group; a substituted or unsubstituted haloalkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bond with an adjacent group to form a substituted or unsubstituted ring; n1 is an integer from 0 to 7, and when n1 is 2 or more, two or more R1s are the same as or different from each other; n2 is an integer from 0 to 9, and when n2 is 2 or more, two or more -L2-R2 are the same as or different from each other; as well as n3 is 1 or 2, and when n3 is 2, the substituents in the two brackets are the same as or different from each other, and 1≤n2+n3≤10, [Chemical formula 2] In chemical formula 2, At least one of X1 to X3 is N, and the rest are CR; R and Ar1 to Ar3 are the same as or different from each other, and are each independently hydrogen; deuterium; cyano; substituted or unsubstituted silyl; substituted or unsubstituted alkyl; substituted or unsubstituted haloalkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group, or bond with an adjacent group to form a substituted or unsubstituted ring, and at least one of Ar1 to Ar3 is represented by the following Chemical Formula 3; L11 to L13 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; and m1 to m3 are each an integer of 0 to 3, and when m1 to m3 are each 2 or more, two or more substituents in brackets are the same as or different from each other, [Chemical formula 3] In chemical formula 3, Any one of R11 to R26 is connected to any one of L11 to L13, and the rest are hydrogen; deuterium; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl, or bonded to an adjacent group to form a substituted or unsubstituted ring, The compound represented by Chemical Formula 2 does not include The organic light-emitting device according to claim 1 , wherein the first organic material layer is a light-emitting layer. 3 . The organic light emitting device according to claim 2 , wherein the light emitting layer comprises one or more types of the compound represented by Chemical Formula 1 as a host of the light emitting layer. The organic light-emitting device according to claim 1 , wherein the second organic material layer is a hole blocking layer or an electron control layer.

5. The organic light emitting device according to claim 1, wherein the compound represented by Chemical Formula 1 is selected from the following structures:

6. The organic light emitting device according to claim 1, wherein the compound represented by Chemical Formula 2 is selected from the following structures: The organic light emitting device according to claim 2 , further comprising one or more light emitting layers.

8. The organic light-emitting device according to claim 2, further comprising one or more light-emitting layers having a maximum light-emitting peak in a wavelength range different from the wavelength range of the maximum light-emitting peak of the light-emitting layer containing one or more types of the compound represented by Chemical Formula 1. 9 . The organic light emitting device according to claim 7 , wherein the light emitting layer including one or more types of the compound represented by Chemical Formula 1 further includes a fluorescent dopant.

10. The organic light-emitting device according to claim 8, wherein one or more light-emitting layers in which the maximum emission peak appears in a wavelength range different from the wavelength range of the maximum emission peak of the light-emitting layer containing one or more types of the compound represented by Chemical Formula 1 contains a phosphorescent dopant.

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