Organic light-emitting devices

Abstract

The present specification provides an organic light-emitting device, which includes: 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 Chemical Formula 1, and the second organic material layer contains a compound represented by Chemical Formula 2.

Description

Technical Field

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0104688 filed in the Korean Intellectual Property Office on September 3, 2018, the entire contents of which are incorporated herein by reference.

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

[0003] The organic light-emitting phenomenon generally refers to the phenomenon of converting electrical energy into light energy using organic materials. An organic light-emitting device utilizing the organic light-emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. In this article, the organic material layer is generally formed in a multilayer structure formed of different materials to improve the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in such an organic light-emitting device structure, holes and electrons are injected into the organic material layer from the anode and the cathode, respectively, and when the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall back to the ground state.

[0004] In the art, aromatic diamine derivatives or aromatic condensed ring diamine derivatives are known as hole transport materials used in organic EL devices. However, since the voltage applied in this case is mostly high, problems such as reduced device life or increased power consumption are caused. In view of these problems, a method for doping an electron accepting compound such as Lewis acid in the hole injection layer of an organic EL device or using the compound alone is proposed. However, it has been shown that the above method has limitations in terms of injecting and transporting holes, and therefore, attempts are made to use a combination of materials between a hole transport layer or a hole control layer or a hole transport layer and a plurality of hole control layers to achieve low voltage, high efficiency and long life effects. The common hole transport layer is a tertiary amine substituted with an aromatic group, and the device characteristics found from the group of combinations of these materials are various. Therefore, it has always been necessary to develop new materials for enhancing the device characteristics obtained by hole transport and carrier control. Summary of the invention

[0005] Technical issues

[0006] The present application aims to provide an organic light-emitting device.

[0007] Technical Solution

[0008] One embodiment of the present application provides an organic light-emitting device, the organic light-emitting device comprising: 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,

[0009] The first organic material layer includes a compound represented by the following Chemical Formula 1:

[0010] The second organic material layer includes a compound represented by the following Chemical Formula 2, and

[0011] The dipole moment value of the second organic material layer is greater than the dipole moment value of the first organic material layer.

[0012] [Chemical formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] At least one of Xa to Xc is N, and the others are CR,

[0016] R is 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 heterocyclyl, and

[0017] Ar2 to Ar4 are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0018] [Chemical formula 2]

[0019] (HAr) a -[L1-Ar1-L2-(CN) b ] c

[0020] In chemical formula 2,

[0021] HAr is a substituted or unsubstituted heterocyclic group containing at least one or more N,

[0022] L1 and L2 are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0023] Ar1 is a direct bond; -O-; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0024] a to c are each an integer from 1 to 3, and

[0025] When a to c are each 2 or greater, two or more structures in brackets are the same as or different from each other.

[0026] Beneficial Effects

[0027] An organic light-emitting device using a compound according to an embodiment of the present application in each of a hole blocking layer, an electron control layer, or an electron transport layer can obtain low driving voltage, high luminous efficiency, or long life. In addition, when the compound satisfies P El >P Eb When the relationship between the amount of electrons transferred to the light-emitting layer is large, the phenomenon of excessive injection of electrons can be controlled, and the organic light-emitting device can obtain high efficiency and long life. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 An example of an organic light-emitting device is shown in which a substrate 1, an anode 2, a light-emitting layer 5, and a cathode 8 are sequentially laminated.

[0029] Figure 2 An example of an organic light emitting device is shown in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, a hole blocking layer or electron control layer 6, an electron injection and transport layer 7 and a cathode 8 are sequentially layered.

[0030] Figure 3 An example of an organic light-emitting device is shown, in which a substrate 1, an anode 2, a first hole injection layer 3a, a first hole transport layer 4a, a first light-emitting layer 5a, a first hole blocking layer 6a, a first electron injection and transport layer 7a, a charge generation layer 9, a second hole injection layer 3b, a second hole transport layer 4b, a second light-emitting layer 5b, a second hole blocking layer 6b, a second electron injection and transport layer 7b and a cathode 8 are sequentially layered.

[0031] [reference numerals]

[0032] 1: Base

[0033] 2: Anode

[0034] 3: Hole injection layer

[0035] 3a: First hole injection layer

[0036] 3b: Second hole injection layer

[0037] 4: Hole transport layer

[0038] 4a: First hole transport layer

[0039] 4b: Second hole transport layer

[0040] 5: Luminous layer

[0041] 5a: First light-emitting layer

[0042] 5b: Second light-emitting layer

[0043] 6: Hole blocking layer or electron control layer

[0044] 6a: First hole blocking layer

[0045] 6b: Second hole blocking layer

[0046] 7: Electron injection and transport layer

[0047] 7a: First electron injection and transport layer

[0048] 7b: Second electron injection and transport layer

[0049] 8: Cathode

[0050] 9: Charge generation layer DETAILED DESCRIPTION

[0051] Hereinafter, the present specification will be described in more detail.

[0052] In the present application, the description that a certain member is placed “on” another member 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.

[0053] In the present application, unless specifically stated otherwise, a description that a part “includes” certain constituent elements means that other constituent elements can also be included, and other constituent elements are not excluded.

[0054] One embodiment of the present application 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 Chemical Formula 1, and the second organic material layer contains a compound represented by Chemical Formula 2.

[0055] According to one embodiment of the present application, the compound represented by Chemical Formula 1 has an advantage of controlling triplet energy by having a core structure as described above, and when each is used as a host compound, characteristics of long life and high efficiency may be obtained.

[0056] Examples of the substituent in the present specification are described below, however, the substituent is not limited thereto.

[0057] 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 may be the same or different from each other.

[0058] In the present specification, the term "substituted or unsubstituted" means substituted by one, 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 two or more substituents connected to each other among the substituents shown above, or having no substituents. For example, "a substituent in which two or more substituents are connected to each other" can be a biphenyl group. In other words, the biphenyl group can be an aryl group, or can be interpreted as a substituent in which two phenyl groups are connected to each other.

[0059] In the present specification, examples of the halogen group may include fluorine, chlorine, bromine or iodine.

[0060] In the present specification, the number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 50. Specifically, a compound having the following structural formula may be included, however, the ester group is not limited thereto.

[0061]

[0062] In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 50. Specifically, a compound having the following structure may be included, however, the carbonyl group is not limited thereto.

[0063]

[0064] In the present specification, the alkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 60. Specific examples thereof may 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, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0065] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. Specific examples thereof may 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, etc., but are not limited thereto.

[0066] In the present specification, the alkoxy group can be linear, 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 may 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, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto.

[0067] In the present specification, the alkenyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 40. Specific examples thereof may 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, stilbene, styryl, and the like, but are not limited thereto.

[0068] In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25. Specific examples of the monocyclic aryl group may include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

[0069] 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 may include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, fluorenyl, etc., but are not limited thereto.

[0070] In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0071] When the fluorenyl group is substituted, it may include Etc. However, the structure is not limited thereto.

[0072] In the present specification, the heterocyclic group is a group containing one or more atoms other than carbon (i.e., 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 may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, thiazolyl, isothiophene Azolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl and the like, but not limited thereto.

[0073] Hereinafter, Chemical Formula 1 will be described in detail.

[0074] According to one embodiment of the present application, at least one of Xa to Xc is N, and the rest are CR.

[0075] According to one embodiment of the present application, Xa is N, and Xb and Xc are CR.

[0076] According to one embodiment of the present application, Xb is N, and Xa and Xc are CR.

[0077] According to one embodiment of the present application, Xc is N, and Xa and Xb are CR.

[0078] According to one embodiment of the present application, Xa and Xb are N, and Xc is CR.

[0079] According to one embodiment of the present application, Xa and Xc are N, and Xb is CR.

[0080] According to one embodiment of the present application, Xb and Xc are N, and Xa is CR.

[0081] According to one embodiment of the present application, Xa to Xc are N.

[0082] According to one embodiment of the present application, R is 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 heterocyclyl.

[0083] According to one embodiment of the present application, R is hydrogen.

[0084] According to one embodiment of the present application, Ar2 to Ar4 are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0085] According to one embodiment of the present application, Ar2 to Ar4 are each independently 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.

[0086] According to one embodiment of the present application, Ar2 to Ar4 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0087] According to one embodiment of the present application, Ar2 to Ar4 are each independently an unsubstituted or substituted aryl group having 6 to 30 carbon atoms: one or more of an alkyl group, an aryl group, and a heterocyclic group, or a group in which two or more thereof are bonded.

[0088] According to one embodiment of the present application, Ar2 to Ar4 are each independently an unsubstituted or substituted aryl 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 one or more of a heterocyclic group having 2 to 30 carbon atoms, or a group in which two or more thereof are bonded.

[0089] According to one embodiment of the present application, Ar2 to Ar4 are each independently an unsubstituted or substituted aryl group having 6 to 30 carbon atoms: any one of a dimethylfluorenyl group, a diphenylfluorenyl group, a spirobifluorenyl group, and a triphenylene group substituted with a phenyl group which is unsubstituted or substituted with a methyl group.

[0090] According to one embodiment of the present application, Ar2 to Ar4 are each independently a phenyl group which is unsubstituted or substituted with any one of dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl and a triphenylene group which is unsubstituted or substituted with a methyl phenyl; a biphenyl group which is unsubstituted or substituted with any one of dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl and a triphenylene group which is unsubstituted or substituted with a methyl phenyl; or a terphenyl group which is unsubstituted or substituted with any one of dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl and a triphenylene group which is unsubstituted or substituted with a methyl phenyl.

[0091] According to one embodiment of the present application, Ar2 to Ar4 are each independently a phenyl group which is unsubstituted or substituted by any one of the following structural formulas; a biphenyl group which is unsubstituted or substituted by any one of the following structural formulas; or a terphenyl group which is unsubstituted or substituted by any one of the following structural formulas.

[0092]

[0093] In the structural formula, the dotted line portion indicates the bonding position.

[0094] According to one embodiment of the present application, at least one of Ar2 to Ar4 is a substituted or unsubstituted heterocyclic group, and the rest are substituted or unsubstituted aryl groups.

[0095] According to one embodiment of the present application, Ar2 to Ar4 are the same as or different from each other, and are each independently represented by -L11-Ar11,

[0096] L11 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group; and

[0097] Ar11 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0098] According to one embodiment of the present application, Ar2 and Ar3 are substituted or unsubstituted aryl groups, and Ar4 is represented by -L11-Ar11.

[0099] According to one embodiment of the present application, Ar2 and Ar4 are substituted or unsubstituted aryl groups, and Ar3 is represented by -L11-Ar11.

[0100] According to one embodiment of the present application, Ar3 and Ar4 are substituted or unsubstituted aryl groups, and Ar2 is represented by -L11-Ar11.

[0101] According to one embodiment of the present application, Ar2 and Ar3 are phenyl groups, and Ar4 is represented by -L11-Ar11.

[0102] According to one embodiment of the present application, Ar2 and Ar4 are phenyl groups, and Ar3 is represented by -L11-Ar11.

[0103] According to one embodiment of the present application, Ar3 and Ar4 are phenyl groups, and Ar2 is represented by -L11-Ar11.

[0104] According to one embodiment of the present application, L11 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0105] According to one embodiment of the present application, L11 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0106] According to one embodiment of the present application, L11 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0107] According to one embodiment of the present application, L11 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted terphenylene group.

[0108] According to one embodiment of the present application, L11 are the same as or different from each other, and are each independently a direct bond; a phenylene group; a biphenylene group; or a terphenylene group.

[0109] According to one embodiment of the present application, L11 are the same as or different from each other, and are each independently a phenylene group; a biphenylene group; or a terphenylene group.

[0110] According to one embodiment of the present application, L11 are the same as or different from each other and are represented by any one of the following structural formulae.

[0111]

[0112] In the structural formula, the dotted line portion indicates the bonding position.

[0113] According to one embodiment of the present application, Ar11 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 heterocyclic group having 2 to 60 carbon atoms.

[0114] According to one embodiment of the present application, Ar11 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0115] According to one embodiment of the present application, Ar11 are the same as or different from each other, and are each independently an aryl group which is unsubstituted or substituted with a group bonded to one or more of an alkyl group and an aryl group, or two or more of which are bonded to each other; or a heterocyclic group which is unsubstituted or substituted with a group bonded to one or more of an alkyl group and an aryl group, or two or more of which are bonded to each other.

[0116] According to one embodiment of the present application, Ar11 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with a group in which one or more of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms, or two or more of which are bonded to each other; or a heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with a group in which one or more of an alkyl group and an aryl group, or two or more of which are bonded to each other.

[0117] According to one embodiment of the present application, Ar11 is the same as or different from each other and is each independently a phenyl group which is unsubstituted or substituted with a group which is bonded to an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms, or two or more thereof; a biphenyl group which is unsubstituted or substituted with a group which is bonded to an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms, or two or more thereof; terphenyl substituted with a group; fluorenyl unsubstituted or substituted with a group bonded to one or more of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms, or two or more thereof; spirobifluorenyl unsubstituted or substituted with a group bonded to one or more of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms, or two or more thereof; triphenylene unsubstituted or substituted with a group bonded to one or more of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms, or two or more thereof; or any one of the following structural formulas.

[0118] According to one embodiment of the present application, Ar11 are the same as or different from each other and are each independently a dimethylfluorenyl group; a diphenylfluorenyl group; a spirobifluorenyl group; a triphenylene group substituted with a phenyl group which is unsubstituted or substituted with a methyl group; or any one of the following structural formulae.

[0119]

[0120] In the structural formula, the dotted line portion indicates the bonding position.

[0121] According to an exemplary embodiment of the present application, Ar11 is represented by any one of the following structural formulae.

[0122]

[0123] In the structural formula, the dotted line portion indicates the bonding position.

[0124] According to one embodiment of the present application, Chemical Formula 1 is represented by the following Chemical Formula 101.

[0125] [Chemical Formula 101]

[0126]

[0127] In Chemical Formula 101, Ar2 to Ar4 have the same definitions as in Chemical Formula 1.

[0128] According to one embodiment of the present application, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3.

[0129] [Chemical formula 1-1]

[0130]

[0131] [Chemical formula 1-2]

[0132]

[0133] [Chemical formula 1-3]

[0134]

[0135] In Chemical Formulas 1-1 to 1-3,

[0136] Xa to Xc, Ar2 and Ar3 have the same definitions as in Chemical Formula 1,

[0137] L is a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted terphenylene group,

[0138] R3, R4, R11, R12, R21 and R22 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imido group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted aromatic substituted or unsubstituted alkylthio; substituted or unsubstituted alkylsulfonyl; substituted or unsubstituted arylsulfonyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; substituted or unsubstituted alkylamino; substituted or unsubstituted aralkylamino; substituted or unsubstituted arylphosphino; or substituted or unsubstituted phosphine oxide, or may be bonded to an adjacent group to form a substituted or unsubstituted ring,

[0139] X1 and X2 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imido group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkylsulfonyl group; a substituted or unsubstituted arylsulfonyl group; acyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; substituted or unsubstituted alkylamino; substituted or unsubstituted aralkylamino; substituted or unsubstituted heteroarylamino; substituted or unsubstituted arylamino; substituted or unsubstituted arylheteroarylamino; substituted or unsubstituted arylphosphino; or substituted or unsubstituted phosphine oxide, or may be bonded to an adjacent group to form a substituted or unsubstituted ring,

[0140] r11 and r12 are the same as or different from each other and are each independently an integer from 0 to 5,

[0141] r21 and r22 are the same as or different from each other and are each independently an integer from 0 to 4,

[0142] m is an integer from 1 to 3,

[0143] d is an integer from 1 to 3,

[0144] e is an integer from 1 to 4, and

[0145] When r11, r12, r21, r22, m, d and e are each 2 or more, the structures in brackets are the same as or different from each other.

[0146] According to one embodiment of the present application, R3, R4, R11, R12, R21 and R22 are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aralkyl; substituted or unsubstituted alkylaryl; substituted or unsubstituted alkylamino; or substituted or unsubstituted aralkylamino, or may be bonded to an adjacent group to form a substituted or unsubstituted ring.

[0147] According to one embodiment of the present specification, R3, R4, R11, R12, R21 and R22 are each independently hydrogen; deuterium; a halogen group; or an alkyl group.

[0148] According to one embodiment of the present specification, R3, R4, R11, R12, R21 and R22 are hydrogen.

[0149] According to one embodiment of the present specification, R3 and R4 are hydrogen.

[0150] According to one embodiment of the present specification, R4 is hydrogen.

[0151] According to one embodiment of the present specification, R3 is hydrogen.

[0152] According to one embodiment of the present specification, L is a phenylene group; a biphenylene group; or a terphenylene group.

[0153] According to one embodiment of the present specification, L is represented by any one of the following structural formulae.

[0154]

[0155] In the structural formula, the dotted line portion indicates the bonding position.

[0156] According to one embodiment of the present application, X1 and X2 are substituted or unsubstituted alkyl groups.

[0157] According to one embodiment of the present application, X1 and X2 are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.

[0158] According to one embodiment of the present application, X1 and X2 are substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms.

[0159] According to one embodiment of the present application, X1 and X2 are substituted or unsubstituted methyl groups.

[0160] According to one embodiment of the present application, X1 and X2 are methyl groups.

[0161] According to one embodiment of the present application, Chemical Formula 1-1 is represented by any one of the following Chemical Formulas 1-1-1 to 1-1-3.

[0162] [Chemical formula 1-1-1]

[0163]

[0164] [Chemical formula 1-1-2]

[0165]

[0166] [Chemical formula 1-1-3]

[0167]

[0168] In Chemical Formulas 1-1-1 to 1-1-3,

[0169] Ar2, Ar3, Xa to Xc, L, R3, R4, R11, R12, r11, r12, m, d and e have the same definitions as in Chemical Formula 1-1.

[0170] According to one embodiment of the present application, Chemical Formula 1-2 is represented by any one of the following Chemical Formulas 1-2-1 to 1-2-3.

[0171] [Chemical formula 1-2-1]

[0172]

[0173] [Chemical formula 1-2-2]

[0174]

[0175] [Chemical formula 1-2-3]

[0176]

[0177] In chemical formulas 1-2-1 to 1-2-3,

[0178] Ar2, Ar3, Xa to Xc, L, R3, R4, R21, R22, r21, r22, m, d and e have the same definitions as in Chemical Formula 1-2.

[0179] According to one embodiment of the present application, Chemical Formula 1-3 is represented by any one of the following Chemical Formulas 1-3-1 to 1-3-3.

[0180] [Chemical formula 1-3-1]

[0181]

[0182] [Chemical formula 1-3-2]

[0183]

[0184] [Chemical formula 1-3-3]

[0185]

[0186] In chemical formulas 1-3-1 to 1-3-3,

[0187] Ar2, Ar3, Xa to Xc, L, R3, R4, X1, X2, m, d and e have the same definitions as in Chemical Formula 1-3.

[0188] According to one embodiment of the present application, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-4 to 1-6.

[0189] [Chemical formula 1-4]

[0190]

[0191] [Chemical formula 1-5]

[0192]

[0193] [Chemical formula 1-6]

[0194]

[0195] In Chemical Formulas 1-4 to 1-6,

[0196] Ar2, Ar3, L, R3, R4, R11, R12, R21, R22, X1, X2, r11, r12, r21, r22, m, d and e have the same definitions as above.

[0197] Hereinafter, Chemical Formula 2 will be described in detail.

[0198] According to one embodiment of the present application, HAr is a substituted or unsubstituted heterocyclic group containing at least one or more N.

[0199] According to one embodiment of the present application, HAr is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and containing at least one or more N.

[0200] According to one embodiment of the present application, HAr is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms and containing at least one or more N.

[0201] According to one embodiment of the present application, HAr is a heterocyclic group containing at least one or more N which is unsubstituted or substituted with an aryl group or a heterocyclic group.

[0202] According to one embodiment of the present application, HAr is a pyridyl group which is unsubstituted or substituted by an aryl group or a heterocyclic group; a pyrimidinyl group which is unsubstituted or substituted by an aryl group or a heterocyclic group; a triazinyl group which is unsubstituted or substituted by an aryl group or a heterocyclic group; or a phenanthroline group which is unsubstituted or substituted by an aryl group or a heterocyclic group.

[0203] According to one embodiment of the present application, HAr is a pyridyl group which is unsubstituted or substituted with one or more of a phenyl group, a biphenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group and a spiro[fluorene-9,9'-xanthene] group; a pyrimidinyl group which is unsubstituted or substituted with one or more of a phenyl group, a biphenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group and a spiro[fluorene-9,9'-xanthene] group; a triazinyl group which is unsubstituted or substituted with a phenyl group, a biphenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group and a spiro[fluorene-9,9'-xanthene] group; or a phenanthroline group.

[0204] According to one embodiment of the present application, HAr is represented by the following Chemical Formula 2-1.

[0205] [Chemical formula 2-1]

[0206]

[0207] In chemical formula 2-1,

[0208] Ar5 and Ar6 are substituted or unsubstituted aryl groups; or substituted or unsubstituted heterocyclic groups, or are bonded with adjacent groups to form a ring; and

[0209] At least one of Xd to Xf is N, and the rest are CH.

[0210] According to one embodiment of the present application, Ar5 and Ar6 are substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or heterocyclic groups having 2 to 60 carbon atoms, or are bonded with adjacent groups to form a ring having 2 to 30 carbon atoms.

[0211] According to one embodiment of the present application, Ar5 and Ar6 are substituted or unsubstituted aryl groups having 6 to 30 carbon atoms; or heterocyclic groups having 2 to 30 carbon atoms, or are bonded with adjacent groups to form a ring having 2 to 20 carbon atoms.

[0212] According to one embodiment of the present application, Ar5 and Ar6 are substituted or unsubstituted aryl groups having 6 to 20 carbon atoms; or heterocyclic groups having 2 to 20 carbon atoms, or are bonded with adjacent groups to form a ring having 2 to 15 carbon atoms.

[0213] According to one embodiment of the present application, Ar5 and Ar6 are substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted fluorenyl; or substituted or unsubstituted spiro[fluorene-9,9'-xanthene]yl, or are bonded to an adjacent group to form a quinone group.

[0214] According to one embodiment of the present application, Ar5 and Ar6 are phenyl; biphenyl; dimethylfluorenyl; diphenylfluorenyl; or spiro[fluorene-9,9′-xanthene]yl.

[0215] According to one embodiment of the present application, Ar5 and Ar6 are phenyl; biphenyl; diphenylfluorenyl; or spiro[fluorene-9,9′-xanthene]yl.

[0216] According to one embodiment of the present application, Ar5 and Ar6 are represented by any one of the following structural formulae.

[0217]

[0218] According to one embodiment of the present application, at least one of Ar2 to Ar4 is a substituted or unsubstituted heterocyclic group, and the rest are substituted or unsubstituted aryl groups.

[0219] In one embodiment of the present application, Xd is N, and the remainder is CH.

[0220] In one embodiment of the present application, Xe is N, and the remainder is CH.

[0221] In one embodiment of the present application, Xf is N, and the remainder is CH.

[0222] In one embodiment of the present application, Xd and Xe are N, and the remainder are CH.

[0223] In one embodiment of the present application, Xd and Xf are N, and the rest are CH.

[0224] In one embodiment of the present application, Xe and Xf are N, and the remainder are CH.

[0225] In one embodiment of the present application, Xd to Xf are N.

[0226] According to one embodiment of the present application, L1 and L2 are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group.

[0227] According to one embodiment of the present application, L1 and L2 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.

[0228] According to one embodiment of the present application, L1 and L2 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.

[0229] According to one embodiment of the present application, L1 and L2 are each independently a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted naphthylene; a substituted or unsubstituted terphenylene; a substituted or unsubstituted fluorenylene; a substituted or unsubstituted divalent dibenzofuranyl; a substituted or unsubstituted divalent dibenzothienyl; or a substituted or unsubstituted divalent spiro[fluorene-9,9'-xanthene] group.

[0230] According to one embodiment of the present application, L1 and L2 are each independently a direct bond; a phenylene group; a biphenylene group; a naphthylene group; a terphenylene group; a dimethylfluorenyl group; a diphenylfluorenyl group; a divalent dibenzofuranyl group; a divalent dibenzothienyl group; or a divalent spiro[fluorene-9,9'-xanthenyl] group, and the substituent may be unsubstituted or substituted with one or more of a cyano group, an aryl group having 6 to 20 carbon atoms, and a heterocyclic group having 2 to 20 carbon atoms, or a group in which two or more thereof are bonded.

[0231] According to one embodiment of the present application, L1 and L2 are each independently a direct bond; a phenylene group; a biphenylene group; a naphthylene group; a terphenylene group; a dimethylfluorenyl group; a diphenylfluorenyl group; a divalent dibenzofuranyl group; a divalent dibenzothienyl group; or a divalent spiro[fluorene-9,9'-xanthenyl] group, and the substituents may be unsubstituted or substituted with one or more of a cyano group, a phenyl group, a biphenyl group, a phenanthryl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a pyridyl group, a pyrimidinyl group and a triazine group, or a group in which two or more thereof are bonded.

[0232] According to one embodiment of the present application, L1 and L2 are each independently a direct bond, or are represented by any one of the following structural formulae.

[0233]

[0234] In the structural formula, the dotted line portion indicates the bonding position.

[0235] In one embodiment of the present specification, Ar1 is a direct bond; -O-; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group.

[0236] In one embodiment of the present specification, Ar1 is a direct bond; -O-; 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.

[0237] In one embodiment of the present specification, Ar1 is a direct bond; -O-; 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.

[0238] In one embodiment of the present specification, Ar1 is a direct bond; -O-; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

[0239] According to one embodiment of the present application, Ar1 is a direct bond; -O-; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted naphthylene; a substituted or unsubstituted terphenylene; a substituted or unsubstituted fluorenylene; a substituted or unsubstituted divalent dibenzofuranyl; a substituted or unsubstituted divalent dibenzothienyl; or a substituted or unsubstituted divalent spiro[fluorene-9,9'-xanthene] group.

[0240] According to one embodiment of the present application, Ar1 is a direct bond; -O-; a phenylene group; a biphenylene group; a naphthylene group; a terphenylene group; a dimethylfluorenyl group; a diphenylfluorenyl group; a divalent dibenzofuranyl group; or a divalent dibenzothiophenyl group, and the substituent is unsubstituted or substituted with one or more of a cyano group, an aryl group having 6 to 20 carbon atoms, and a heterocyclic group having 2 to 20 carbon atoms, or a group in which two or more thereof are bonded.

[0241] According to one embodiment of the present application, Ar1 is a direct bond; -O-; a direct bond; a phenylene group; a biphenylene group; a naphthylene group; a terphenylene group; a dimethylfluorenyl group; a diphenylfluorenyl group; a divalent dibenzofuranyl group; a divalent dibenzothienyl group; or a divalent spiro[fluorene-9,9'-xanthenyl] group, and the substituent is unsubstituted or substituted with one or more of a cyano group, a phenyl group, a biphenyl group, a phenanthryl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a pyridyl group, a pyrimidinyl group and a triazine group, or a group bonded with two or more thereof.

[0242] According to one embodiment of the present application, Ar1 is each independently a direct bond; or -O-, or is represented by any one of the following structural formulae.

[0243]

[0244] In the structural formula, the dotted line portion indicates the bonding position.

[0245] In one embodiment of the present specification, a to c are each an integer of 1 to 3, and when a to c is 2 or more, two or more structures in brackets are the same as or different from each other.

[0246] In one embodiment of the present specification, a is 1 or 2.

[0247] In one embodiment of the present specification, b is 1 or 2.

[0248] In one embodiment of the present specification, c is 1 or 2.

[0249] In addition, in one embodiment of the present application, Chemical Formula 1 may be selected from the following structural formulas.

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263] In addition, in one embodiment of the present application, Chemical Formula 2 is selected from the following structural formulas.

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279] According to one embodiment of the present specification, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 satisfy the following Formula 1.

[0280] [Formula 1]

[0281] |P El |>|P Eb |

[0282] In formula 1,

[0283] |P Eb | means the absolute value of the dipole moment of the compound represented by Chemical Formula 1, and

[0284] |P El | means the absolute value of the dipole moment of the compound represented by Chemical Formula 2.

[0285] According to one embodiment of the present specification, the dipole moment is a physical quantity representing the degree of polarity and can be calculated by the following Mathematical Equation 1.

[0286] [Mathematical equation 1]

[0287]

[0288] ·ρ(r 0 ): molecular density

[0289] V: Volume

[0290] r: observation point

[0291] ·d 3 r 0 : Volume unit

[0292] In Mathematical Equation 1, the dipole moment value can be obtained by obtaining the molecular density through calculation. For example, after obtaining the charge and dipole of each atom using the Hirshfeld charge analysis method, the molecular density can be obtained by calculation according to the following equation, and the calculation result can be substituted into Mathematical Equation 1 to obtain the dipole moment.

[0293] Weight function

[0294]

[0295] ·ρ α (rR α ): spherical average ground state atomic density

[0296] · : Promolecule density

[0297] Deformation density

[0298]

[0299] ρ(t): molecular density

[0300] ·ρ α (rR α ): located at coordinate R α The density of free atoms α at

[0301] Atomic charge

[0302] q(α)=-∫ρ d (r)W α (r)d 3 r

[0303] ·W d (r): weight function

[0304] According to one embodiment of the present specification, the structure of Chemical Formula 2 includes a cyano group capable of significantly increasing a dipole moment without significantly affecting the overall molecular shape, while the structure of Chemical Formula 1 does not include a cyano group.

[0305] Therefore, the dipole moment of Chemical Formula 2 containing a cyano group is greatly increased, and the second organic material layer containing the Chemical Formula 2 and the first organic material layer containing the Chemical Formula 1 not containing a cyano group satisfy Equation 1, resulting in a large dipole moment and a difference in LUMO energy level. This acts as a barrier between the second organic material layer and the first organic material layer, thereby controlling the amount and rate of electrons injected from the cathode into the light-emitting layer, and thus obtaining an effect of improving the life of the organic light-emitting device.

[0306] The first organic material layer and the second organic material layer of the organic light-emitting device of the present application may be formed as a single-layer structure, but may also be formed as a multilayer structure in which two or more organic material layers are laminated. For example, the first organic material layer of the present application may be formed as one to three layers. In addition, the organic light-emitting device of the present application may have a structure including a hole injection layer, a light-emitting layer, an electron transport layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a larger number or a smaller number of organic layers.

[0307] In one embodiment of the present application, the organic light-emitting device further includes one, two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.

[0308] In one embodiment of the present application, an organic light-emitting device includes a first electrode; a second electrode arranged opposite to the first electrode; two or more light-emitting layers arranged between the first electrode and the second electrode; and two or more first organic material layers and second organic material layers arranged between the two or more light-emitting layers and the first electrode, or between the two or more light-emitting layers and the second electrode, wherein the two or more first organic material layers and the second organic material layers respectively contain a compound represented by Chemical Formula 1 or a compound represented by Chemical Formula 2.

[0309] According to one embodiment of the present application, the first organic material layer includes a hole blocking layer or an electron control layer, the second organic material layer includes an electron transport layer, and the hole blocking layer or the electron control layer contains a compound represented by Chemical Formula 1, and the electron transport layer may contain a compound represented by Chemical Formula 2.

[0310] In one embodiment of the present application, in addition to the organic material layer containing the compound, the first organic material layer and the second organic material layer further include: a hole injection layer or a hole transport layer containing a compound containing an arylamino group, a carbazole group or a benzocarbazole group.

[0311] In another embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially laminated on a substrate.

[0312] In another embodiment, the organic light emitting device may be an organic light emitting device having a reverse structure (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially laminated on a substrate.

[0313] For example, Figures 1 to 3 Schematic diagram of a structure of an organic light-emitting device according to an embodiment of the present application.

[0314] Figure 1 1 shows the structure of a general organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 5, and a cathode 8 are sequentially laminated. Figure 1 When, the organic light-emitting device according to one embodiment of the present application may include two or more light-emitting layers. In addition, the light-emitting layers may each independently include a fluorescent dopant or a phosphorescent dopant. When there are two light-emitting layers, one light-emitting layer may include a fluorescent dopant, and the other may include a phosphorescent dopant.

[0315] In addition, according to one embodiment of the present application, two or more light-emitting layers may be arranged in a vertical direction from the first electrode to the second electrode, or may be arranged in a horizontal direction from the first electrode to the second electrode.

[0316] Figure 2 The structure of such an organic light-emitting device is shown, in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, a hole blocking layer or an electron control layer 6, an electron injection and transport layer 7 and a cathode 8 are sequentially laminated. Figure 2 When the OLED device according to one embodiment of the present application includes three or more emitting layers, other layers may be provided between the emitting layers. When the emitting layers are provided as three or more layers, the emitting layers may each include a blue fluorescent emitting layer. Figure 2 In the structure of , the compound represented by Chemical Formula 1 may be included in the hole blocking layer or the electron control layer 6 , and the compound represented by Chemical Formula 2 may be included in the electron injection and transport layer 7 .

[0317] According to one embodiment of the present application, three or more light emitting layers may be sequentially disposed in a direction from the first electrode to the second electrode.

[0318] In addition, according to one embodiment of the present application, three or more light-emitting layers may be arranged in a vertical direction from the first electrode to the second electrode, or may be arranged in a horizontal direction from the first electrode to the second electrode. More specifically, three or more light-emitting layers may be arranged in a horizontal direction from the first electrode to the second electrode.

[0319] According to one embodiment of the present application, the blue fluorescent light-emitting layer includes a host and a dopant, and the host may be any one selected from the following structures.

[0320]

[0321]

[0322] According to one embodiment of the present specification, the organic light emitting device may have a series structure in which two or more independent devices are connected in series. In one embodiment, the series structure may have a form in which each organic light emitting device is combined through a charge generation layer. Compared with a unit device based on the same brightness, the device of the series structure can be driven at a lower current, which has the advantage of greatly improving the life characteristics of the device.

[0323] According to one embodiment of the present specification, the organic material layer includes: a first stack including one or more light-emitting layers; a second stack including one or more light-emitting layers; and one or more charge generation layers disposed between the first stack and the second stack.

[0324] According to another embodiment of the present specification, the organic material layer includes: a first stack including one or more light-emitting layers; a second stack including one or more light-emitting layers; and a third stack including one or more light-emitting layers, and includes: one or more charge generating layers each between the first stack and the second stack and between the second stack and the third stack.

[0325] In this specification, the charge generation layer means a layer that generates holes and electrons when a voltage is applied. The charge generation layer may be an N-type charge generation layer or a P-type charge generation layer. In this specification, the N-type charge generation layer means a charge generation layer that is positioned closer to the anode than the P-type charge generation layer, and the P-type charge generation layer means a charge generation layer that is positioned closer to the cathode than the N-type charge generation layer.

[0326] The N-type charge generation layer and the P-type charge generation layer may be arranged in contact with each other, and in this case, an NP junction is formed. Through the NP junction, holes are easily formed in the P-type charge generation layer, and electrons are easily formed in the N-type charge generation layer. Electrons are transmitted to the anode direction through the LUMO energy level of the N-type charge generation layer, and holes are transmitted to the cathode direction through the HOMO energy level of the P-type organic material layer.

[0327] The first stack, the second stack and the third stack each include one or more light-emitting layers, and in addition, may also include one or more layers of a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a layer that simultaneously performs hole transport and hole injection (hole injection and transport layer), and a layer that simultaneously performs electron transport and electron injection (electron injection and transport layer).

[0328] Figure 3 An organic light emitting device including a first stack and a second stack is shown in FIG.

[0329] Figure 3An organic light-emitting device is shown in which a substrate 1, an anode 2, a first hole injection layer 3a, a first hole transport layer 4a, a first light-emitting layer 5a, a first hole blocking layer 6a, a first electron injection and transport layer 7a, a charge generation layer 9, a second hole injection layer 3b, a second hole transport layer 4b, a second light-emitting layer 5b, a second hole blocking layer 6b, a second electron injection and transport layer 7b, and a cathode 8 are sequentially laminated. In such a structure, the compound represented by Chemical Formula 1 may be contained in the first hole blocking layer 6a or the second hole blocking layer 6b, and the compound represented by Chemical Formula 2 may be contained in the first electron injection and transport layer 7a or the second electron injection and transport layer 7b.

[0330] The N-type charge generation layer may include 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylene derivatives, etc., but is not limited thereto. In one embodiment, the N-type charge generation layer may include both benzimidazolophenanthridine-based derivatives and Li metal.

[0331] The P-type charge generation layer may contain both the arylamine-based derivative and the cyano group-containing compound.

[0332] The organic light-emitting device of the present application can be manufactured using materials and methods known in the art, except that one or more layers of the first organic material layer or the second organic material layer contain the compound of the present application, ie, the above-mentioned compound.

[0333] When the organic light emitting device includes a plurality of first organic material layers or second organic material layers, the organic material layers may be formed of materials that are the same as or different from each other.

[0334] The organic light-emitting device of the present application can be manufactured using materials and methods known in the art, except that one or more of the first organic material layer and the second organic material layer contains the above-mentioned compound, that is, the compound represented by any one of Chemical Formulas 1 and 2.

[0335] For example, the organic light-emitting device of the present application can be manufactured by sequentially laminating a first electrode, a first organic material layer, a second organic material layer, and a second electrode on a substrate. In this article, the organic light-emitting device can be manufactured by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method (such as sputtering or electron beam evaporation) to form an anode on a substrate, forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport 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, an 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.

[0336] In addition, when manufacturing an organic light-emitting device, the compounds of Chemical Formulas 1 and 2 can be formed into an organic material layer using a solution coating method and a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0337] In addition to such a method, an 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 (International Patent Application Laid-Open No. 2003 / 012890). However, the manufacturing method is not limited thereto.

[0338] In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.

[0339] In another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0340] As the anode material, a material having a large work function is generally preferred so that hole injection 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 SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, etc., but not limited thereto.

[0341] As the cathode material, a material having a small work function is generally preferred so that electron injection is smooth. Specific examples of the cathode 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 LiO 2 / Al; and so on, but not limited to.

[0342] 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 in the anode and excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and in addition, has excellent film forming ability. 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 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, and conductive polymers based on polyaniline and polythiophene, but are not limited thereto.

[0343] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. As the 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 mobility for holes is suitable. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both a conjugated portion and a non-conjugated portion, etc., but are not limited thereto.

[0344] The luminescent material is a material that can emit light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and electrons, and is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); carbazole-based compounds; diphenylethylene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoquinoline-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.

[0345] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. As the electron transport material, a material that can smoothly receive electrons from the cathode and move the electrons to the light-emitting layer and has high mobility for electrons is suitable. In addition to the compound represented by Chemical Formula 2, specific examples thereof include Al complexes of 8-hydroxyquinoline; Alq 3The electron transport layer may be used together with any desired cathode material as used in the art. In particular, examples of suitable cathode materials include common materials having a small work function and followed by an aluminum layer or a silver layer. Specifically, the cathode material includes cesium, barium, calcium, ytterbium and samarium, and in each case is followed by an aluminum layer or a silver layer.

[0346] 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 cathode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the hole injection layer, and, in addition, has an excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone and the like and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but not limited thereto.

[0347] 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.

[0348] The hole blocking layer is a layer that blocks holes from reaching the cathode, and generally, can be formed under the same conditions as the hole injection layer. Specifically, in addition to the compound represented by Chemical Formula 1, Oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., however, the material is not limited thereto.

[0349] 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 used.

[0350] Embodiments of the invention

[0351] The manufacture of an organic light-emitting device including the compounds represented by Chemical Formula 1 and Chemical Formula 2 will be specifically described in the following examples. However, the following examples are for illustrative purposes only, and the scope of the present specification is not limited thereto.

[0352] Preparation Example 1: Preparation of Compound EC1

[0353]

[0354] After compound EC1-A (10 g, 36.6 mmol) and compound EC1-B (18.7 g, 36.6 mmol) were completely dissolved in tetrahydrofuran (200 mL), potassium carbonate (15.2 g, 109.8 mmol) dissolved in water (60 mL) was added thereto. Tetrakis triphenylphosphine palladium (1.37 g, 0.110 mmol) was introduced thereto, and the resultant was stirred for 8 hours while heating. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed to filter the white solid. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate respectively to prepare compound EC1 (16.9 g, yield 80%).

[0355] MS[M+H] + =578

[0356] Preparation Example 2: Preparation of Compound EC2

[0357]

[0358] A compound represented by Chemical Formula EC2 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as respective starting materials.

[0359] MS[M+H] + =626

[0360] Preparation Example 3: Preparation of Compound EC3

[0361]

[0362] A compound represented by Chemical Formula EC3 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as respective starting materials.

[0363] MS[M+H] + =698

[0364] Preparation Example 4: Preparation of Compound EC4

[0365]

[0366] A compound represented by Chemical Formula EC4 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as respective starting materials.

[0367] MS[M+H] + =665

[0368] Preparation Example 5: Preparation of Compound EC5

[0369]

[0370] A compound represented by Chemical Formula EC5 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as each starting material.

[0371] MS[M+H] + =689

[0372] Preparation Example 6: Preparation of Compound ET1

[0373]

[0374] A compound represented by Chemical Formula ET1 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as respective starting materials.

[0375] MS[M+H] + =613

[0376] Preparation Example 7: Preparation of Compound ET2

[0377]

[0378] A compound represented by Chemical Formula ET2 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as respective starting materials.

[0379] MS[M+H] + =562

[0380] Preparation Example 8: Preparation of Compound ET3

[0381]

[0382] A compound represented by Chemical Formula ET3 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as respective starting materials.

[0383] MS[M+H] + =758

[0384] Preparation Example 9: Preparation of Compound ET4

[0385]

[0386] A compound represented by Chemical Formula ET4 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as respective starting materials.

[0387] MS[M+H] + =727

[0388] Preparation Example 10: Preparation of Compound ET5

[0389]

[0390] A compound represented by Chemical Formula ET5 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as respective starting materials.

[0391] MS[M+H] + =653

[0392] Preparation Example 11: Preparation of Compound ET6

[0393]

[0394] A compound represented by Chemical Formula ET6 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as respective starting materials.

[0395] MS[M+H] + =665

[0396] Preparation Example 12: Preparation of Compound ET7

[0397]

[0398] A compound represented by Chemical Formula ET7 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as respective starting materials.

[0399] MS[M+H] + =651

[0400] Preparation Example 13: Preparation of Compound ET8

[0401]

[0402] A compound represented by Chemical Formula ET8 was prepared in the same manner as in Preparation Example 1, except that the above-mentioned compounds were used as respective starting materials.

[0403] MS[M+H] + =563

[0404] Example 1-1

[0405] It is coated with a thickness of Indium tin oxide (ITO) of the present invention is put into the distilled water dissolved with cleaning agent and carries out ultrasonic cleaning as the glass substrate of film.In this article, use the product of Fischer Co. as cleaning agent, and as distilled water, use the distilled water filtered twice by the filter manufactured by Millipore Co..After ITO was cleaned for 30 minutes, use distilled water to repeat twice ultrasonic cleaning for 10 minutes.After finishing with distilled water cleaning, use isopropyl alcohol, acetone and methanol solvent to carry out ultrasonic cleaning to substrate, then dry, then transfer it to plasma cleaner.In addition, use oxygen plasma to clean substrate for 5 minutes, then transfer it to vacuum deposition device.

[0406] On the transparent ITO electrode prepared as above, the following HI-A compound was thermally vacuum deposited onto The hole injection layer is formed by vacuum depositing the following HAT compounds in a continuous order: and the following HT-A compounds A hole transport layer is formed on the hole injection layer.

[0407] Subsequently, a light-emitting layer was formed on the hole transport layer by vacuum depositing the following BH compound and the following BD compound in a weight ratio of 25:1. The film thickness.

[0408] By vacuum deposition of compound EC1 onto A hole blocking layer is formed on the light-emitting layer with a thickness of 1:1. On the hole blocking layer, a mixture of compound ET1 and the following LiQ compound is vacuum deposited in a weight ratio of 1:1 to The electron injection and transport layer is formed by sequentially depositing a layer having a thickness of of lithium fluoride (LiF) and a thickness of The aluminum forms a cathode on the electron injection and transport layer.

[0409] During the above process, the deposition rate of the organic material is maintained at / second to / sec, and the deposition rates of lithium fluoride and aluminum at the cathode were kept at / second and / sec, and the vacuum degree during deposition was maintained at 1 × 10 -7 Up to 5×10 -5 Thus, an organic light emitting device is manufactured.

[0410]

[0411] Examples 1-2 to 1-24 and Comparative Examples 1-1 to 1-14

[0412] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compounds of the following Table 1 were used instead of Compounds EC1 and ET1.

[0413] For the organic light-emitting devices manufactured in Examples 1-1 to 1-24 and Comparative Examples 1-1 to 1-14, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time (T90) taken for the luminance to decrease to 90% compared to its initial luminance was measured at a current density of 1.5 Å. The results are shown in Table 1 below.

[0414] [Table 1]

[0415]

[0416]

[0417] As can be seen from Table 1, the organic light emitting device using both Chemical Formula 1 and Chemical Formula 2 according to the present specification exhibits characteristics of low driving voltage, high efficiency, and long life, compared with the organic light emitting device using only Chemical Formula 1 or only Chemical Formula 2. In particular, it is determined that the life of Examples 1-1 to 1-24 increases by up to about 660% compared with Comparative Examples 1-1 to 1-14.

[0418] Example 2-1

[0419] It is coated with a thickness of Indium tin oxide (ITO) of the present invention is put into the distilled water dissolved with cleaning agent and carries out ultrasonic cleaning as the glass substrate of film.In this article, use the product of Fischer Co. as cleaning agent, and as distilled water, use the distilled water filtered twice by the filter manufactured by Millipore Co..After ITO was cleaned for 30 minutes, use distilled water to repeat twice ultrasonic cleaning for 10 minutes.After finishing with distilled water cleaning, use isopropyl alcohol, acetone and methanol solvent to carry out ultrasonic cleaning to substrate, then dry, then transfer it to plasma cleaner.In addition, use oxygen plasma to clean substrate for 5 minutes, then transfer it to vacuum deposition device.

[0420] On the transparent ITO electrode prepared as above, the following HI-A compound was thermally vacuum deposited onto The first hole injection layer is formed by vacuum depositing the following HAT compounds in a continuous order: and the following HT-A compounds A first hole transport layer is formed on the first hole injection layer.

[0421] Subsequently, a first light-emitting layer was formed on the first hole transport layer by vacuum depositing the following BH compound and the following BD compound in a weight ratio of 25:1 to The film thickness.

[0422] By vacuum deposition of compound EC1 onto A first hole blocking layer is formed on the first light-emitting layer with a thickness of 1:1. On the first hole blocking layer, a compound ET1 and the following LiQ compound are vacuum deposited in a weight ratio of 1:1 to A first electron injection and transport layer is formed with a thickness of

[0423] The compound ET-C and the lithium compound were vacuum deposited in a weight ratio of 100:2. An electron charge generation layer was formed on the first electron injection and transport layer with a film thickness of . On the electron charge generation layer, the following HI-A compound was thermally vacuum deposited onto A second hole injection layer is formed with a thickness of

[0424] By vacuum depositing the following HAT compounds in sequential order and the following HT-A compounds A second hole transport layer is formed on the second hole injection layer.

[0425] Subsequently, the following BH compound and the following BD compound were vacuum deposited at a weight ratio of 25:1 onto A second light-emitting layer is formed on the second hole transport layer with a film thickness of .

[0426] By vacuum deposition of compound EC1 onto A second hole blocking layer is formed on the second light emitting layer with a thickness of 1:1. On the second hole blocking layer, a compound ET1 and the following LiQ compound are vacuum deposited in a weight ratio of 1:1 to The second electron injection and transport layer is formed by sequentially depositing of lithium fluoride (LiF) and a thickness of A cathode is formed on the second electron injection and transport layer.

[0427] During the above process, the deposition rate of the organic material is maintained at / second to / sec, and the deposition rates of lithium fluoride and aluminum at the cathode were kept at / second and / sec, and the vacuum degree during deposition was maintained at 1 × 10 -7 Up to 5×10 -5 Thus, an organic light emitting device is manufactured.

[0428]

[0429] Examples 2-2 to 2-24 and Comparative Examples 2-1 to 2-14

[0430] An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the compounds of the following Table 2 were used instead of Compounds EC1 and ET1.

[0431] For the organic light-emitting devices manufactured in Examples 2-1 to 2-24 and Comparative Examples 2-1 to 2-14, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time (T90) taken for the luminance to decrease to 90% compared to its initial luminance was measured at a current density of 1.5 Å. The results are shown in Table 2 below.

[0432] [Table 2]

[0433]

[0434]

[0435] As can be seen from Table 2, the organic light-emitting device using both Chemical Formula 1 and Chemical Formula 2 according to the present specification exhibits characteristics of low driving voltage, high efficiency, and long life, compared with the organic light-emitting device using only Chemical Formula 1 or only Chemical Formula 2. In particular, it is determined that the life of Examples 2-1 to 2-24 increases by up to about 680% compared with Comparative Examples 2-1 to 2-14.

[0436] Example 3

[0437] The dipole moment (Debye) values ​​of Chemical Formulas EC1 to EC5, ET1 to ET8, and ET-A according to one embodiment of the present specification are listed in the following Table 3.

[0438] [Table 3]

[0439] Chemical formula Dipole moment (Debye) EC1 0.70 EC2 0.93 EC3 0.22 EC4 2.54 EC5 2.69 ET1 3.83 ET2 5.28 ET3 5.78 ET4 6.02 ET5 4.66 ET6 5.38 ET7 5.89 ET8 5.54 ET-A 3.61

[0440] The quantum chemical calculation program Gaussian 03 manufactured by Gaussian, Inc. of the United States was used and the density functional theory (DFT) was used to obtain the dipole moment (Debye), and the calculated value of the triplet energy was obtained by using the time-dependent density functional theory (TD-DFT) for optimizing the structure using B3LYP as the functional and 6-31G* as the basis function. The P in Table 3 El >P EbThe relationship between the amount of electrons transferred to the light-emitting layer can control the phenomenon of excessive injection, thereby obtaining high efficiency and long life in the organic light-emitting device.

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, The first organic material layer is a hole blocking layer or an electron control layer, The second organic material layer is an electron transport layer or an electron injection and transport layer, The first organic material layer includes a compound represented by the following Chemical Formula 1: The second organic material layer includes a compound represented by the following Chemical Formula 2, and The dipole moment value of the second organic material layer is greater than the dipole moment value of the first organic material layer: [Chemical formula 1] In Chemical Formula 1, At least one of Xa to Xc is N, and the others are CR; R is hydrogen; Ar2 and Ar3 are phenyl groups; Ar4 is represented by -L11-Ar11; L11 is phenylene; or biphenylene; Ar11 is dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl or any one of the following structural formulas: [Chemical formula 2] (HAr) a -[L1-Ar1-L2-(CN) b , c In chemical formula 2, HAr is represented by the following chemical formula 2-1: [Chemical formula 2-1] In chemical formula 2-1, Ar5 and Ar6 are phenyl groups; Xd to Xf are N; L1 and L2 are each independently a direct bond; a phenylene group; a biphenylene group; or a naphthylene group; Ar1 is a direct bond; a phenylene group; a biphenylene group; a naphthylene group; or is represented by any of the following structural formulas: a to c are each an integer from 1 to 2; and When a to c are each 2, the structures in the two brackets are the same as or different from each other.

2. The organic light emitting device according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 101: [Chemical Formula 101] In Chemical Formula 101, Ar2 to Ar4 have the same definitions as in Chemical Formula 1.

3. The organic light-emitting device according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] In Chemical Formulas 1-1 to 1-3, Xa to Xc, Ar2 and Ar3 have the same definitions as in Chemical Formula 1; L is phenylene; or biphenylene; R3, R4, R11, R12, R21 and R22 are hydrogen; X1 and X2 are the same as or different from each other and are each independently a methyl group; r11 and r12 are the same as or different from each other, and are each independently an integer from 0 to 5; r21 and r22 are the same as or different from each other, and are each independently an integer from 0 to 4; m is an integer from 1 to 3; d is an integer from 1 to 3; e is an integer from 1 to 4; and When r11, r12, r21, r22, m, d and e are each 2 or more, the structures in brackets are the same as or different from each other.

4. The organic light emitting device according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-4 to 1-6: [Chemical formula 1-4] [Chemical formula 1-5] [Chemical formula 1-6] In Chemical Formulas 1-4 to 1-6, Ar2 and Ar3 have the same definitions as in Chemical Formula 1; L is phenylene; or biphenylene; R3, R4, R11, R12, R21 and R22 are hydrogen; X1 and X2 are the same as or different from each other and are each independently a methyl group; r11 and r12 are the same or different from each other and are each independently an integer from 0 to 5; r21 and r22 are the same or different from each other and are each independently an integer from 0 to 4; m is an integer from 1 to 3; d is an integer from 1 to 3; e is an integer from 1 to 4; and When r11, r12, r21, r22, m, d and e are each 2 or more, the structures in brackets are the same as or different from each other.

5. The organic light emitting device according to claim 1, wherein the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 satisfy the following Formula 1: [Formula 1] |P El |>|P Eb | In formula 1, |P Eb | means the absolute value of the dipole moment of the compound represented by Chemical Formula 1; and |P El | means the absolute value of the dipole moment of the compound represented by Chemical Formula 2. The organic light emitting device according to claim 1 , wherein the first organic material layer is a hole blocking layer. The organic light-emitting device according to claim 1 , wherein the second organic material layer is an electron transport layer. 8 . The organic light emitting device according to claim 1 , comprising two or more light emitting layers between the first electrode and the second electrode, wherein the light emitting layers each independently contain a fluorescent dopant or a phosphorescent dopant. 9 . The organic light emitting device according to claim 1 , comprising three or more light emitting layers between the first electrode and the second electrode, wherein the light emitting layers each comprise a blue fluorescent light emitting layer. 10 . The organic light emitting device according to claim 9 , wherein the three or more light emitting layers are sequentially disposed in a direction from the first electrode to the second electrode.

11. 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, The first organic material layer is a hole blocking layer or an electron control layer, the second organic material layer is an electron transport layer or an electron injection and transport layer, and the first organic material layer comprises a compound selected from the following: The second organic material layer includes a compound represented by the following Chemical Formula 2: [Chemical formula 2] (HAr) a -[L1-Ar1-L2-(CN) b , c In chemical formula 2, HAr is represented by the following chemical formula 2-1: [Chemical formula 2-1] In chemical formula 2-1, Ar5 and Ar6 are phenyl groups; Xd to Xf are N; L1 and L2 are each independently a direct bond; a phenylene group; a biphenylene group; or a naphthylene group; Ar1 is a direct bond; a phenylene group; a biphenylene group; a naphthylene group; or is represented by any of the following structural formulas: a to c are each an integer from 1 to 2; and When a to c are each 2, the structures in the two brackets are the same as or different from each other, and The dipole moment value of the second organic material layer is greater than the dipole moment value of the first organic material layer.

12. 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, The first organic material layer is a hole blocking layer or an electron control layer, The second organic material layer is an electron transport layer or an electron injection and transport layer, The first organic material layer comprises a compound represented by the following Chemical Formula 1: [Chemical formula 1] In Chemical Formula 1, At least one of Xa to Xc is N, and the others are CR; R is hydrogen; Ar2 and Ar3 are phenyl groups; Ar4 is represented by -L11-Ar11; L11 is phenylene; or biphenylene; Ar11 is dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl or any one of the following structural formulas: The second organic material layer comprises a compound selected from the following: as well as The dipole moment value of the second organic material layer is greater than the dipole moment value of the first organic material layer.

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