Organic Light Emitting Diodes

Abstract

The present specification provides an organic light-emitting device including the compounds represented by Formula 1 and Formula 2.

Description

Technical Field

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0097023 filed in the Korean Intellectual Property Office on August 20, 2018, the entire contents of which are incorporated herein by reference.

[0002] The present application relates to organic light emitting devices. Background Art

[0003] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. An organic light-emitting device utilizing the organic light-emitting phenomenon generally has a structure including a positive electrode, a negative electrode, and an organic material layer therebetween. Here, the organic material layer has a multilayer structure composed of different materials in many cases to improve the efficiency and stability of the organic light-emitting device, and for example, the organic material layer may be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, if a voltage is applied between the two electrodes, holes are injected into the organic material layer from the positive electrode, and electrons are injected into the organic material layer from the negative electrode, and when the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall to the ground state again.

[0004] There is a continuing need to develop new materials for the aforementioned organic light-emitting devices. Summary of the invention

[0005] Technical issues

[0006] The present application relates to organic light emitting devices.

[0007] Technical Solution

[0008] The present application is dedicated to providing such an organic light-emitting device, which includes: a first electrode; a second electrode arranged to face the first electrode; and an organic material layer having one or more layers arranged between the first electrode and the second electrode.

[0009] wherein a compound represented by the following Formula 1 is contained as a host in an organic material layer having one or more layers, and

[0010] A compound represented by the following Formula 2 is included as a dopant in an organic material layer having one or more layers.

[0011] [Formula 1]

[0012]

[0013] In formula 1,

[0014] L is a phenylene group which is unsubstituted or substituted with one or more substituents selected from aryl and deuterium,

[0015] Ar1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0016] R1 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0017] R2 and R3 are the same as or different from each other and are each independently hydrogen; or deuterium,

[0018] a is an integer from 1 to 5,

[0019] b is an integer from 1 to 8,

[0020] c is an integer from 1 to 4,

[0021] d is an integer from 1 to 5,

[0022] When a is 2 or more, two or more Ar1 are the same as or different from each other,

[0023] When b is 2 or more, two or more R1 are the same as or different from each other,

[0024] When c is 2 or more, two or more R2 are the same as or different from each other, and

[0025] When d is 2 or more, two or more R3 are the same as or different from each other,

[0026] [Formula 2]

[0027]

[0028] In formula 2,

[0029] A, E and C are each a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring,

[0030] Y1 is boron; or phosphine oxide,

[0031] X1 and X2 are each O; or NR,

[0032] R is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0033] Adjacent groups among R, E and C may be bonded to each other to form a ring.

[0034] Beneficial Effects

[0035] An organic light emitting device using the compound according to an exemplary embodiment of the present application may have low driving voltage, high light emitting efficiency, and / or a long lifetime. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 An example of an organic light-emitting device in which a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4 are sequentially stacked is shown.

[0037] Figure 2 An example of an organic light-emitting device in which a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7, and a negative electrode 4 are sequentially stacked is shown.

[0038] [Explanation of Reference Numerals]

[0039] 1: Base

[0040] 2: Positive electrode

[0041] 3: Luminous layer

[0042] 4: Negative electrode

[0043] 5: Hole injection layer

[0044] 6: Hole transport layer

[0045] 7: Electron transport layer DETAILED DESCRIPTION

[0046] Hereinafter, the present specification will be described in more detail.

[0047] The present specification provides an organic light-emitting device including the compounds represented by Formula 1 and Formula 2.

[0048] Specifically, an exemplary embodiment of the present specification includes a compound represented by Formula 1 (including anthracene) as a host, and includes a compound represented by Formula 2 (including boron) as a dopant. When the compounds represented by Formula 1 and Formula 2 are used in an appropriate ratio to form a light-emitting layer, deep blue light emission can be generated and high light emission efficiency can be exhibited. In addition, the emission wavelength of the compound containing anthracene and the absorption wavelength of the compound containing boron frequently overlap, so that energy is easily transferred from the host to the dopant.

[0049] In the case of the compound represented by Formula 1, the 9- and 10-positions of anthracene are substituted with phenylene groups, thereby exhibiting an effect of further improving luminous efficiency compared to the case where the 9- and 10-positions of anthracene are substituted with naphthylene groups.

[0050] Examples of the substituent in the present specification will be described below, but are not limited thereto.

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

[0052] In the present specification, the term "substituted or unsubstituted" means substituted by one or two or more substituents selected from the following: hydrogen; halogen group; nitrile group; nitro group; hydroxyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic group, or substituted by a substituent in which two or more substituents are connected among the substituents exemplified above, or having no substituent. For example, "a substituent in which two or more substituents are connected" can be a biphenyl group. That is, the biphenyl group can also be an aryl group, and can be interpreted as a substituent in which two phenyl groups are connected.

[0053] In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

[0054] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 50. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0055] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0056] In the present specification, the alkoxy group may be straight chain, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but are not limited thereto.

[0057] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, phenyl group, styryl group, etc., but are not limited thereto.

[0058] In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 6 to 25. Specific examples of the monocyclic aryl group include phenyl, biphenyl, terphenyl and the like, but are not limited thereto.

[0059] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 24. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, fluorenyl, etc., but are not limited thereto.

[0060] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0061] When the fluorenyl group is substituted, the substituent may be etc., but not limited to.

[0062] In the present specification, the heterocyclic group contains one or more atoms other than carbon, that is, one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl and the like, but are not limited thereto.

[0063] In the present specification, the above description of the aryl group can be applied to the aromatic hydrocarbon ring, except that the aromatic hydrocarbon ring is a divalent group.

[0064] In the present specification, the above description of the heterocyclic group can be applied to the heterocycle, except that the heterocycle is a divalent group.

[0065] In the present specification, the substituted or unsubstituted aromatic hydrocarbon ring is a divalent or higher-valent group.

[0066] In the present specification, a substituted or unsubstituted heterocycle is a divalent or higher-valent group.

[0067] In the present specification, the above description of the aryl group can be applied to the aryl group of the arylamine group.

[0068] In the present specification, the meaning of bonding with an adjacent group to form a ring means bonding with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, or a substituted or unsubstituted aromatic heterocycle.

[0069] In the present specification, the aliphatic hydrocarbon ring means a ring which is a ring of a non-aromatic group composed of only carbon and hydrogen atoms.

[0070] In the present specification, examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, and the like, but are not limited thereto.

[0071] In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more hetero atoms.

[0072] In the present specification, an aromatic heterocycle means an aromatic ring containing one or more heteroatoms.

[0073] In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

[0074] In this specification, an "adjacent" group may mean a substituent that replaces an atom directly connected to the atom replaced by the corresponding substituent, a substituent that is arranged closest to the corresponding substituent in space, or another substituent that replaces the atom replaced by the corresponding substituent. For example, two substituents substituted at the ortho position of a benzene ring and two substituents that replace the same carbon in an aliphatic ring may be understood as groups "adjacent" to each other.

[0075] In the present specification, the case where adjacent groups are bonded to each other to form a ring means that the adjacent groups are bonded to each other to form a 5-membered to 8-membered hydrocarbon ring or a 5-membered to 8-membered heterocycle as described above, and the ring may be a monocyclic or polycyclic ring, and may be an aliphatic ring, an aromatic ring, or a condensed form thereof, and is not limited thereto.

[0076] According to an exemplary embodiment of the present application, L is a phenylene group which is unsubstituted or substituted with one or more substituents selected from an aryl group and deuterium.

[0077] According to an exemplary embodiment of the present application, L is a phenylene group which is unsubstituted or substituted with one or more substituents selected from phenyl, naphthyl, and deuterium.

[0078] According to an exemplary embodiment of the present application, L is a phenylene group which is unsubstituted or substituted with a substituent selected from a phenyl group, a naphthyl group, and a deuterium group.

[0079] According to an exemplary embodiment of the present application, L is a phenylene group substituted with a phenyl group; a phenylene group substituted with a naphthyl group; a phenylene group substituted with a deuterium group; or a phenylene group.

[0080] According to an exemplary embodiment of the present application, Ar1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0081] In addition, according to an exemplary embodiment of the present application, Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 60 carbon atoms.

[0082] In addition, according to an exemplary embodiment of the present application, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.

[0083] According to an exemplary embodiment of the present application, Ar1 is a substituted or unsubstituted aryl group; a dibenzofuranyl group; a dibenzothienyl group; or a substituted or unsubstituted carbazolyl group.

[0084] According to an exemplary embodiment of the present application, Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted triphenylene group; a dibenzofuranyl group; a dibenzothienyl group; or a substituted or unsubstituted carbazolyl group.

[0085] According to an exemplary embodiment of the present application, Ar1 is an unsubstituted or deuterium-substituted phenyl group; an unsubstituted or deuterium-substituted naphthyl group; an unsubstituted or deuterium-substituted phenanthryl group; an unsubstituted or deuterium-substituted pyrene group; an unsubstituted or deuterium-substituted triphenylene group; a dibenzofuranyl group; a dibenzothienyl group; or an unsubstituted or phenyl-substituted carbazolyl group.

[0086] According to an exemplary embodiment of the present application, a is an integer of 1 to 5.

[0087] According to an exemplary embodiment of the present application, a is 1 or 2.

[0088] According to an exemplary embodiment of the present application, R1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0089] According to an exemplary embodiment of the present application, R1 is hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0090] According to an exemplary embodiment of the present application, R1 is hydrogen or deuterium.

[0091] According to an exemplary embodiment of the present application, b is an integer of 1 to 8.

[0092] According to an exemplary embodiment of the present application, b is 8.

[0093] According to an exemplary embodiment of the present application, R2 and R3 are the same as or different from each other, and are each independently hydrogen; or deuterium.

[0094] According to an exemplary embodiment of the present application, c is an integer of 1 to 4.

[0095] According to an exemplary embodiment of the present application, c is 4.

[0096] According to an exemplary embodiment of the present application, d is an integer of 1 to 5.

[0097] According to an exemplary embodiment of the present application, d is 5.

[0098] According to an exemplary embodiment of the present application, A, E and C are each a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring.

[0099] According to an exemplary embodiment of the present application, A, E, and C are each a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic ring having 3 to 60 carbon atoms.

[0100] According to an exemplary embodiment of the present application, A, E, and C are each a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic ring having 3 to 30 carbon atoms.

[0101] According to an exemplary embodiment of the present application, A, E and C are each an aromatic hydrocarbon ring which is unsubstituted or substituted with one or more substituents selected from an alkyl group, an amine group and a heterocyclic group; or a heterocyclic ring which is unsubstituted or substituted with one or more substituents selected from an alkyl group, an amine group and a heterocyclic group.

[0102] According to an exemplary embodiment of the present application, A, E and C are each an aromatic hydrocarbon ring having 6 to 30 carbon atoms which is unsubstituted or substituted with one or more substituents selected from alkyl, amine and heterocyclic groups; or a heterocycle having 3 to 30 carbon atoms which is unsubstituted or substituted with one or more substituents selected from alkyl, amine and heterocyclic groups.

[0103] According to an exemplary embodiment of the present application, A, E, and C are each a substituted or unsubstituted divalent or higher-valent aryl group; or a substituted or unsubstituted divalent or higher-valent heterocyclic group.

[0104] According to an exemplary embodiment of the present application, A, E, and C are each a substituted or unsubstituted divalent aromatic group; or a substituted or unsubstituted divalent heterocyclic group.

[0105] According to an exemplary embodiment of the present application, A, E and C are each phenyl which is unsubstituted or substituted with one or more substituents selected from alkyl, amine and heterocyclic groups; naphthyl which is unsubstituted or substituted with one or more substituents selected from alkyl, amine and heterocyclic groups; or dibenzofuranyl which is unsubstituted or substituted with one or more substituents selected from alkyl, amine and heterocyclic groups. In this case, phenyl, naphthyl and dibenzofuranyl may be divalent or higher.

[0106] According to an exemplary embodiment of the present application, Y1 is boron or phosphine oxide.

[0107] According to an exemplary embodiment of the present application, Y1 is boron.

[0108] According to an exemplary embodiment of the present application, X1 and X2 are each O; or NR.

[0109] According to an exemplary embodiment of the present application, R is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0110] According to an exemplary embodiment of the present application, R is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0111] According to an exemplary embodiment of the present application, R is a substituted or unsubstituted aryl group.

[0112] According to an exemplary embodiment of the present application, R is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

[0113] According to an exemplary embodiment of the present application, R is an unsubstituted or alkyl-substituted phenyl group; or an unsubstituted or alkyl-substituted naphthyl group.

[0114] According to an exemplary embodiment of the present application, R is an unsubstituted or alkyl-substituted phenyl group; or a naphthyl group.

[0115] According to an exemplary embodiment of the present application, adjacent groups among R, E, and C may be bonded to each other to form a ring.

[0116] According to an exemplary embodiment of the present application, adjacent groups among R, E, and C may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring.

[0117] According to an exemplary embodiment of the present application, adjacent groups among R, E, and C may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.

[0118] According to an exemplary embodiment of the present application, adjacent groups among R, E, and C may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.

[0119] Formula 2 of the present application is represented by the following Formula 2-1.

[0120] [Formula 2-1]

[0121]

[0122] In formula 2-1,

[0123] The definitions of A, E and C are the same as those defined in Formula 2,

[0124] R' and R" are each independently substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclyl; and

[0125] Adjacent groups among R′, E, C, and R″ may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring.

[0126] According to an exemplary embodiment of the present application, Formula 1 is selected from the following structural formulas.

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] According to an exemplary embodiment of the present application, Formula 2 is selected from the following structural formulas.

[0134]

[0135]

[0136] According to an exemplary embodiment of the present application, the organic material layer includes Formula 1 and Formula 2, and Formula 1 and Formula 2 are included in a weight ratio of 90:10 to 99:1 (Formula 1: Formula 2). Preferably, Formula 1 and Formula 2 are included in a weight ratio of 99:1 to 95:5.

[0137] The core structure of Formula 1 according to an exemplary embodiment of the present specification can be prepared as shown in the following Reaction Formula 1, the substituents can be bonded by methods known in the art, and the type, position or number of the substituents can be changed according to techniques known in the art.

[0138] <Reaction formula 1>

[0139]

[0140] In Reaction Formula 1, the definitions of R1 to R3, L and Ar1 are the same as those defined in Formula 1 above.

[0141] The core structure of Formula 2 according to an exemplary embodiment of the present specification can be prepared as shown in the following Reaction Formula 2, the substituents can be bonded by methods known in the art, and the type, position or number of the substituents can be changed according to techniques known in the art.

[0142] <Reaction 2>

[0143]

[0144] In Reaction Formula 2, the definitions of A, E, C, X1, X2 and Y1 are the same as those defined in Formula 2 above.

[0145] In the present application, when one member is disposed “on” another member, this includes not only a case where one member is in contact with another member but also a case where another member exists between the two members.

[0146] In the present application, when a part “includes” a constituent element, unless specifically described otherwise, this does not mean that another constituent element is excluded but means that another constituent element may further be included.

[0147] The organic material layer of the organic light-emitting device of the present application may also be composed of a single-layer structure, but may also be composed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0148] In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously injects and transports holes contains the compounds represented by Formula 1 and Formula 2.

[0149] In an exemplary embodiment of the present application, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Formula 1.

[0150] In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 2.

[0151] In yet another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 and the compound represented by Formula 2.

[0152] In an exemplary embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons contains compounds represented by Formula 1 and Formula 2.

[0153] In an exemplary embodiment of the present application, the organic light-emitting device further includes one or two or more layers selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

[0154] In an exemplary embodiment of the present application, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Formula 1 as a host.

[0155] In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 2 as a blue dopant.

[0156] The light-emitting layer may include an additional host in addition to the compound represented by Formula 1. Examples of additional host materials include fused aromatic ring derivatives, heterocyclic compounds, etc. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and specific examples of heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but examples are not limited thereto.

[0157] In an exemplary embodiment of the present application, the thickness of the organic material layer including the compound represented by Formula 1 is to

[0158] In an exemplary embodiment of the present application, the organic light emitting device may be a normal type organic light emitting device in which a positive electrode, an organic material layer having one or more layers, and a negative electrode are sequentially stacked on a substrate.

[0159] In another exemplary embodiment, the organic light emitting device may be an inverted organic light emitting device in which a negative electrode, an organic material layer having one or more layers, and a positive electrode are sequentially stacked on a substrate.

[0160] For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present application is illustrated in Figure 1 and Figure 2 middle.

[0161] Figure 1 The structure of an organic light emitting device is illustrated in which a substrate 1, a positive electrode 2, a light emitting layer 3, and a negative electrode 4 are sequentially stacked. In the above structure, the compound may be contained in the light emitting layer 3.

[0162] Figure 2 The structure of an organic light emitting device in which a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a negative electrode 4 are sequentially stacked is illustrated.

[0163] In an exemplary embodiment of the present specification, the organic light emitting device may have a structure in which a substrate, a positive electrode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a negative electrode are sequentially stacked.

[0164] In the above structure, the compounds of Formula 1 and Formula 2 may each be included in one or more layers of a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.

[0165] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0166] The organic light-emitting device of the present application can be manufactured by materials and methods known in the art, except that one or more layers of the organic material layer contain the compound, ie, the compound represented by Formula 1 and the compound represented by Formula 2.

[0167] For example, the organic light-emitting device of the present application can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured by the following process: a metal or a conductive metal oxide, or an alloy thereof is deposited on a substrate using a physical vapor deposition (PVD) method (such as sputtering or electron beam evaporation) to form a positive electrode, an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the positive electrode, and then a material that can be used as a negative electrode is deposited on the organic material layer. In addition to the above method, the organic light-emitting device can also be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate.

[0168] In addition, when manufacturing an organic light-emitting device, the compounds of Formula 1 and Formula 2 can be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, doctor blade coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited thereto.

[0169] In addition to the above method, an organic light emitting device can also be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate (International Publication No. 2003 / 012890). However, the manufacturing method is not limited thereto.

[0170] In an exemplary embodiment of the present application, the first electrode is a positive electrode, and the second electrode is a negative electrode.

[0171] In another exemplary embodiment, the first electrode is a negative electrode and the second electrode is a positive electrode.

[0172] As the positive electrode material, a material with a high work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention 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; etc., but are not limited thereto.

[0173] As the negative electrode material, a material with a low work function is generally preferred to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material 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; etc., but are not limited thereto.

[0174] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, and therefore has the effect of injecting holes at the positive electrode and the excellent effect of injecting holes into the light-emitting layer or the light-emitting material, preventing the excitons generated by the light-emitting layer from moving to the electron injection layer or the electron injection material, and also has excellent film forming ability. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the positive electrode material and the HOMO of the adjacent organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, conductive polymers based on polyaniline and polythiophene, etc., but are not limited thereto.

[0175] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is appropriately a material having high hole mobility that can receive holes from the positive electrode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0176] The luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region, and is preferably a material having high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based azoles, benzothiazole-based and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene, and the like, but are not limited thereto.

[0177] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer, and the electron transport material is appropriately a material with high electron mobility that can advantageously receive electrons from the negative electrode and transfer the electrons to the light-emitting layer. 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. The electron transport layer can be used with any desired cathode material as used according to the relevant technology. In particular, suitable examples of cathode materials are typical materials with low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium, and samarium, in each case followed by an aluminum layer or a silver layer.

[0178] The electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound that has the ability to transport electrons, has an effect of injecting electrons from the negative electrode and an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated by the light-emitting layer from moving to the hole injection layer, and also has excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but not limited thereto.

[0179] Examples of 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.

[0180] The hole blocking layer is a layer that blocks holes from reaching the negative electrode and can generally be formed under the same conditions as those of the hole injection layer. Specific examples of the hole blocking material include Oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but not limited thereto.

[0181] The organic light emitting device according to the present application may be a top emission type, a bottom emission type, or a dual emission type according to the materials to be used.

[0182] Embodiments of the invention

[0183] Hereinafter, the present specification will be described in detail with reference to the embodiments for specifically describing the present specification. However, the embodiments according to the present specification can be modified in various forms, and should not be interpreted as limiting the scope of the present specification to the embodiments described in detail below. The embodiments of the present specification are provided to explain the present specification more comprehensively to those of ordinary skill in the art.

[0184] <Synthesis example>

[0185] Synthesis Example 1. Synthesis of Compound 1

[0186] 9-Bromoanthracene (1 equivalent), 4-biphenylboronic acid (1.1 equivalent), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.1 equivalent) and potassium carbonate (K2CO3) (3 equivalents) were dissolved in tetrahydrofuran (THF) and water in a ratio of 3:1, and the resulting solution was refluxed under heating. After the reaction was completed, the resulting product was extracted with toluene, washed with water, and then recrystallized with toluene to obtain compound 9-([1,1′-biphenyl]-4-yl)anthracene in a yield of 85%. The prepared compound was identified by a mass spectrometer [cal.m / s: 330.4, exp.m / s(M+) 329.5].

[0187] 9-([1,1′-biphenyl]-4-yl)anthracene (1 equivalent) was dissolved in THF, N-bromosuccinimide (1 equivalent) was dissolved in dimethylformamide (DMF) and the resulting solution was slowly added dropwise thereto at room temperature. After the reaction was completed, a solid produced by adding an excess of water thereto was filtered to obtain compound 9-([1,1′-biphenyl]-4-yl)-10-bromoanthracene in a yield of 87%. The prepared compound was identified by a mass spectrometer [cal.m / s: 409.3, exp.m / s (M+) 408.5].

[0188] 9-([1,1′-biphenyl]-4-yl)-10-bromoanthracene (1 equivalent), (3-(naphthalene-1-yl)phenyl)boric acid (1.1 equivalent), Pd(PPh3)4 (0.1 equivalent) and K2CO3 (3 equivalents) were dissolved in tetrahydrofuran (THF) and water in a ratio of 3:1, and the resulting solution was refluxed under heating. After the reaction was completed, the resulting product was extracted with toluene, washed with water, and then recrystallized with toluene to obtain the following compound 1 with a yield of 81%. The prepared compound was identified by a mass spectrometer [cal.m / s: 532.2, exp.m / s (M+) 531.2].

[0189] In Synthesis Example 1 and the following Synthesis Examples, cal.m / s is a calculated value of the mass of the prepared compound, and exp.m / s means a measurement result obtained by actual mass spectrometry of the prepared compound.

[0190] For mass spectrometry, Expression-S with Plate Express model manufactured by Advion, Inc. was used, and measurement was performed on a sample dissolved in THF at a concentration of 1 mg / 2 ml.

[0191] Synthesis Examples 2 to 12. Synthesis of Compounds 2 to 12

[0192] Compounds 2 to 12 were obtained in the same manner as in Synthesis Example 1, except that the compounds in Table 1 below were used instead of 4-biphenylboronic acid and (3-(naphthalen-1-yl)phenyl)boronic acid in Synthesis Example 1.

[0193] By subjecting the compounds prepared in Synthesis Examples 1 to 12 to mass analysis, it was confirmed that the compounds were prepared, and the measurement results thereof are shown in Table 1 below.

[0194] [Table 1]

[0195]

[0196] Compounds 1 to 12 prepared as described above are as follows.

[0197]

[0198] Synthesis Examples 13 to 16. Synthesis of Compounds 13 to 16

[0199] The following compounds 13 to 16 were synthesized by the method detailed in US Pat. No. 8,890,131 B2.

[0200]

[0201] By subjecting the compounds prepared in Synthesis Examples 13 to 16 to mass analysis, it was confirmed that the compounds were prepared, and the measurement results thereof are shown in Table 2 below.

[0202] [Table 2]

[0203] Compound cal.m / s exp.m / s 1 3 612.4 606～611 1 4 508.3 500～505 15 560.3 558～560 16 560.3 558～560

[0204] During the polymerization reaction to prepare the deuterium-substituted compound, it was found that compounds in which all substitutable positions were substituted with deuterium and compounds in which a part of the substitutable positions were not substituted with deuterium were produced, and thus the exp m / s value was distributed.

[0205] Synthesis Example 17. Synthesis of BD-1

[0206] After placing intermediate 1,3-dibromo-5-chlorobenzene (1 equivalent), bis(4-(tert-butyl)phenyl)amine (3.0 equivalents), sodium tert-butoxide (3 equivalents) and bis(tri(tert-butyl)phosphine)palladium(0) (0.05 equivalents) in toluene under a nitrogen atmosphere, the resulting solution was heated and stirred at 120° C. for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, separated by adding water and NH4Cl aqueous solution thereto, and then filtered by treating with anhydrous magnesium sulfate (anhydrous MgSO4). The filtered solution was distilled off under reduced pressure and purified by recrystallization to obtain N1,N1,N3,N3-tetrakis(4-(tert-butyl)phenyl)-5-chlorobenzene-1,3-diamine in a yield of 58%.

[0207] Under nitrogen atmosphere, N1,N1,N3,N3-tetrakis(4-(tert-butyl)phenyl)-5-chlorobenzene-1,3-diamine (1 equivalent) and BI3 (1.5 equivalents) were dissolved in dichlorobenzene, and the resulting solution was stirred at 130° C. for 3 hours. After the reaction was completed, the reaction solution was cooled to room temperature, extracted, and then filtered by treating with anhydrous MgSO4. The filtered solution was distilled off under reduced pressure, column purified (toluene / hexane), and then recrystallized to obtain 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-chloro-5,9-dihydro-5,9-diaza-13b-boronaphtho[3,2,1-de]anthracene in a yield of 65%.

[0208] After placing the intermediate 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-chloro-5,9-dihydro-5,9-diaza-13b-boronaphtho[3,2,1-de]anthracene (1 equivalent), diphenylamine (1.5 equivalents), sodium tert-butoxide (2 equivalents) and bis(tri(tert-butyl)phosphine)palladium(0) (0.03 equivalents) in toluene under a nitrogen atmosphere, the resulting solution was heated at 120° C. and stirred for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, separated by adding water and an NH4Cl aqueous solution thereto, and then filtered by treating with anhydrous MgSO4. The filtered solution was distilled off under reduced pressure and purified by recrystallization to obtain the following compound BD-1 with a yield of 68%. The final compound was determined by a mass spectrometer [cai.m / s: 811.97, exp.m / s (M+) 810.6].

[0209]

[0210] Example 1

[0211] The glass substrate thinly coated with the indium tin oxide (ITO) with a thickness of 150nm is placed in the distilled water dissolved with a detergent, and ultrasonic cleaning is performed. In this case, the product manufactured by Fischer Co. is used as a detergent, and the distilled water filtered twice using the filter manufactured by Millipore Co. is used as distilled water. After ITO was washed for 30 minutes, ultrasonic cleaning was repeated twice using distilled water for 10 minutes. After the distilled water washing is completed, ultrasonic cleaning is performed by using isopropanol, acetone and methanol solvents, and the products therefrom are dried and then transported to a plasma scrubber. In addition, nitrogen plasma is used to wash the substrate for 5 minutes, and then it is transported to a vacuum depositor. On the ITO transparent electrode prepared in this way, the following HAT-CN compound is deposited by thermal vacuum deposition to a thickness of 5nm, thereby forming a hole injection layer. Subsequently, the following HTL1 of thermal vacuum deposition to a thickness of 100nm, and then the following HTL2 of thermal vacuum deposition to a thickness of 10nm, thereby forming a hole transport layer. Subsequently, compound 1 as a host and BD-1 as a dopant (weight ratio 95:3) were simultaneously vacuum deposited to form a light-emitting layer with a thickness of 20 nm. Subsequently, the following ETL was vacuum deposited to a thickness of 20 nm to form an electron transport layer. Subsequently, LiF was vacuum deposited to a thickness of 0.5 nm to form an electron injection layer. Subsequently, aluminum was deposited to a thickness of 100 nm to form a negative electrode, thereby manufacturing an organic light-emitting device.

[0212]

[0213] Examples 2 to 16

[0214] An organic light emitting device was manufactured in the same manner as in Example 1, except that the materials (as a host and a dopant) and contents (based on 1 part by weight of the combination of the host and the dopant) of the following Table 3 were used.

[0215] [Table 3]

[0216]

[0217] Comparative Examples 1 to 6

[0218] An organic light emitting device was manufactured in the same manner as in Example 1, except that the materials (as a host and a dopant) and contents (based on 1 part by weight of the combination of the host and the dopant) of the following Table 4 were used.

[0219] [Table 4]

[0220]

[0221]

[0222] Comparative Examples 7 to 28

[0223] An organic light emitting device was manufactured in the same manner as in Example 1, except that the materials (as a host and a dopant) and contents (based on 1 part by weight of the combination of the host and the dopant) of the following Table 5 were used.

[0224] The structure of BD-2 used in Comparative Examples 7 to 28 is as follows.

[0225]

[0226] [Table 5]

[0227]

[0228] At 10mA / cm 2 The current efficiency (cd / A) and luminous efficiency of the organic light-emitting devices manufactured in Examples 1 to 16 and Comparative Examples 1 to 28 were measured at a current density of 20 mA / cm 2 The time (LT) when the luminance became 95% compared with the initial luminance was measured at a current density of , and the results are shown in Tables 6 to 8 below.

[0229] [Table 6]

[0230]

[0231] [Table 7]

[0232]

[0233] [Table 8]

[0234]

[0235] When comparing Table 6 and Table 7, it can be determined that the case where the compound in which both the 9-position and the 10-position of anthracene are substituted by phenylene (the compound represented by Formula 1) is used as the main body (Examples 1 to 12) is better than the case where the compound in which at least one of the 9-position and the 10-position of anthracene is substituted by other substituents other than phenylene is used as the main body (Comparative Examples 1 to 6).

[0236] In particular, it was confirmed that in the case of the deuterium-substituted compounds among the compounds represented by Formula 1 (Examples 13 to 16), the stability of the molecule was improved, and the lifetime of the device was greatly improved.

[0237] When Table 6 is compared with Table 8, it can be determined that when the compound represented by Formula 2 is not included as a dopant, the current efficiency and service life of the device are reduced even if the compound represented by Formula 1 is included as a host (Comparative Examples 7 to 18 and Comparative Examples 25 to 28).

[0238] It can be confirmed that excellent performance is exhibited only when the compound represented by Formula 1 is included as a host and the compound represented by Formula 2 is included as a dopant.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode disposed facing the first electrode; as well as an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein a compound represented by the following Formula 1 is contained as a main body in the organic material layer having one or more layers, and A compound represented by the following Formula 2 is included as a dopant in the organic material layer having one or more layers: [Formula 1] In formula 1, L is a phenylene group which is unsubstituted or substituted with one or more substituents selected from a monocyclic aromatic group having 6 to 25 carbon atoms, a polycyclic aromatic group having 10 to 24 carbon atoms, and deuterium, Ar1 is unsubstituted or deuterium-substituted phenyl; unsubstituted biphenyl; unsubstituted or deuterium-substituted naphthyl; unsubstituted anthracenyl; unsubstituted or deuterium-substituted phenanthrenyl; unsubstituted or deuterium-substituted pyrenyl; unsubstituted or deuterium-substituted triphenylene; substituted or unsubstituted fluorenyl; or a substituted or unsubstituted heterocyclic group having 3 to 60 carbon atoms, R1 is hydrogen; or deuterium, R2 and R3 are the same as or different from each other and are each independently hydrogen; or deuterium, a is an integer from 1 to 5, b is an integer from 1 to 8, c is an integer from 1 to 4, d is an integer from 1 to 5, When a is 2 or more, two or more Ar1 are the same as or different from each other, When b is 2 or more, two or more R1 are the same as or different from each other, When c is 2 or more, two or more R2 are the same as or different from each other, and When d is 2 or more, two or more R3 are the same as or different from each other, [Formula 2] In formula 2, A, E and C are each a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic ring having 3 to 60 carbon atoms, Y1 is boron, X1 and X2 are each O; or NR, R is a substituted or unsubstituted monocyclic aromatic group having 6 to 25 carbon atoms, or a substituted or unsubstituted polycyclic aromatic group having 10 to 24 carbon atoms, and Adjacent groups among R, E and C are optionally bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms, The substituted or unsubstituted means substituted with one or two or more substituents selected from the following: an alkyl group having 1 to 50 carbon atoms, an amine group, a monocyclic aromatic group having 6 to 25 carbon atoms, a polycyclic aromatic group having 10 to 24 carbon atoms, and a heterocyclic group having 2 to 60 carbon atoms, or substituted with a substituent in which two or more substituents among the substituents are connected, or has no substituent.

2. The organic light-emitting device according to claim 1, wherein Ar1 is an unsubstituted or deuterium-substituted phenyl group; an unsubstituted biphenyl group; an unsubstituted or deuterium-substituted naphthyl group; an unsubstituted anthracenyl group; an unsubstituted or deuterium-substituted phenanthrenyl group; an unsubstituted or deuterium-substituted pyrene group; an unsubstituted or deuterium-substituted triphenylene group; a dibenzofuranyl group; a dibenzothienyl group; or an unsubstituted or phenyl-substituted carbazolyl group.

3. An organic light-emitting device, comprising: a first electrode; a second electrode disposed facing the first electrode; as well as an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein a compound represented by the following structural formula is contained as a main component in the organic material layer having one or more layers, and A compound represented by the following Formula 2 is included as a dopant in the organic material layer having one or more layers: [Structural formula] [Formula 2] In formula 2, A, E and C are each a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic ring having 3 to 60 carbon atoms, Y1 is boron, X1 and X2 are each O; or NR, R is a substituted or unsubstituted monocyclic aromatic group having 6 to 25 carbon atoms, or a substituted or unsubstituted polycyclic aromatic group having 10 to 24 carbon atoms, and Adjacent groups among R, E and C are optionally bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms, The substituted or unsubstituted means substituted with one or two or more substituents selected from the following: an alkyl group having 1 to 50 carbon atoms, an amine group, a monocyclic aromatic group having 6 to 25 carbon atoms, a polycyclic aromatic group having 10 to 24 carbon atoms, and a heterocyclic group having 2 to 60 carbon atoms, or substituted with a substituent in which two or more substituents among the substituents are connected, or has no substituent.

4. The organic light-emitting device according to claim 1, wherein Formula 2 is selected from the following structural formulas: 5 . The organic light emitting device according to claim 1 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compounds represented by Formula 1 and Formula 2.

6. An organic light-emitting device according to claim 1, wherein the organic material layer comprises an electron injection layer, an electron transport layer, or a layer for simultaneously injecting and transporting electrons, and the electron injection layer, the electron transport layer, or the layer for simultaneously injecting and transporting electrons contains compounds represented by Formula 1 and Formula 2.

7. An organic light-emitting device according to claim 1, wherein the organic material layer includes a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously injects and transports holes contains compounds represented by Formula 1 and Formula 2. 8 . The organic light emitting device according to claim 1 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound represented by Formula 2 as a blue dopant.

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