Organic light-emitting devices

Abstract

The present specification relates to an organic light-emitting device, which includes: a first electrode; a second electrode arranged opposite to the first electrode; and an organic material layer arranged between the first electrode and the second electrode, wherein the organic material layer includes a hole transport layer and an electron blocking layer, and the hole transport layer and the electron blocking layer contain a compound of Chemical Formula 1, the materials of the hole transport layer and the electron blocking layer are different from each other, and one or more layers of the organic material layer that are not the hole transport layer and the electron blocking layer contain a compound of Chemical Formula 2.

Description

Technical Field

[0001] This disclosure claims priority to and the benefit of Korean Patent Application No. 10-2018-0112912, filed on September 20, 2018, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

[0002] This specification 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, in order to improve the efficiency and stability of the organic light-emitting device, the organic material layer is generally formed in a multilayer structure formed of different materials. 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 from the anode and cathode into the organic material layer, 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] There is an ongoing need to develop new materials for such organic light emitting devices. Summary of the invention

[0005] Technical issues

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

[0007] Technical Solution

[0008] One embodiment of the present specification provides an organic light emitting device, the organic light emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and an organic material layer disposed between the first electrode and the second electrode,

[0009] The organic material layer includes a hole transport layer and an electron blocking layer, and the hole transport layer and the electron blocking layer include a compound of the following chemical formula 1;

[0010] The materials of the hole transport layer and the electron blocking layer are different from each other; and

[0011] One or more layers that are neither the hole transport layer nor the electron blocking layer in the organic material layer include a compound of the following Chemical Formula 2:

[0012] [Chemical formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] Ar1 and Ar2 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group containing one or two 6-membered rings, or a substituted or unsubstituted heteroaryl group,

[0016] a and b are the same as or different from each other and are each independently a substituted or unsubstituted aromatic ring,

[0017] X1 and X2 are the same as or different from each other and are each independently a direct bond or CRR'; and

[0018] When one of X1 and X2 is a direct key, the other is CRR',

[0019] [Chemical formula 2]

[0020]

[0021] In chemical formula 2,

[0022] Ar3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0023] L is a substituted or unsubstituted arylene group,

[0024] R, R', R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring,

[0025] c is an integer from 0 to 8,

[0026] d is an integer from 0 to 7,

[0027] When c is a plural number, R1 are the same or different from each other, and

[0028] When d is a plural number, R2's are the same as or different from each other.

[0029] Beneficial Effects

[0030] An organic light emitting device according to one embodiment of the present specification has the advantages of low voltage, high efficiency, and long lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1 An organic light emitting device according to one embodiment of the present specification is shown.

[0032] Figure 2 An organic light emitting device according to one embodiment of the present specification is shown.

[0033] Figure 3An organic light emitting device according to one embodiment of the present specification is shown.

[0034] [reference numerals]

[0035] 1: Base

[0036] 2: First electrode

[0037] 3: Organic material layer

[0038] 4: Second electrode

[0039] 5: Hole injection layer

[0040] 6: Hole transport layer

[0041] 7: Electron blocking layer

[0042] 8: Luminous layer

[0043] 9: Electron transport layer

[0044] 10: Electron injection layer DETAILED DESCRIPTION

[0045] Hereinafter, the present specification will be described in more detail.

[0046] When the compound represented by Chemical Formula 1 of the present disclosure is used in the hole transport layer and the electron blocking layer, since the interface characteristics between the hole transport layer and the electron blocking layer become excellent due to similar structures, characteristics that are conducive to hole injection and migration can be obtained. Generally, the hole transport layer in contact with the hole injection layer requires a higher HOMO energy level than the electron blocking layer, and the electron blocking layer requires a high triplet energy. When the substitution position of the amine group in the structure of Chemical Formula 1 is changed, the HOMO energy level, triplet energy, etc. can be controlled to be different, and the appropriate characteristics required for each layer can be met. Therefore, when the two layers contain the same material, the characteristics required for each layer may not be met, and when only any one layer uses the compound of Chemical Formula 1, the voltage may increase due to the reduction of the interface characteristics, but when the compounds of Chemical Formula 1 different from each other are used in the hole transport layer and the electron blocking layer, such problems can be completely overcome, and when used in an organic electroluminescent device, low voltage and high efficiency characteristics can be obtained. When the compound represented by Chemical Formula 1 of the present disclosure is used in the hole transport layer and the electron blocking layer, compared to when the compound represented by Chemical Formula 1 of the present disclosure is used in each of the hole transport layer, the electron blocking layer and the light emitting layer, since the structures of the compounds used in the two layers are similar, characteristics conducive to hole injection and migration can be obtained.

[0047] In particular, when the compound is used in each layer while changing the substitution position of the amine group, the characteristics can be controlled to be characteristics suitable for the role of each layer.

[0048] In addition, when the structure of Chemical Formula 2 is used as a host material, the angles between anthracene and L and between L and naphthyl in Chemical Formula 2 are perpendicular, the conjugation length can be controlled to be short, and the distance between anthracenes accumulated by extending the molecule can be kept close, which is beneficial to charge transfer.

[0049] In the fused aryl group, as the number of fused rings increases, the triplet energy decreases. Since the structure of Chemical Formula 2 used as the host of the light-emitting layer includes an anthracene structure, when the structure of Chemical Formula 1 includes a functional group containing three or more 6-membered rings such as anthracene, the triplet energy may be smaller than that of the light-emitting layer host.

[0050] Even when the structure of Chemical Formula 1 of the present disclosure is maintained, a material used as an electron blocking layer needs to have a larger triplet energy than a host material of the light emitting layer to function as a blocking layer.

[0051] In the present application, unless specifically described to the contrary, a description that a part “includes” certain constituent elements means that additional constituent elements can also be included, and other constituent elements are not excluded.

[0052] In the present application, the description that a certain member is disposed “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] Examples of the substituent in the present specification are described below, however, the substituent is not limited thereto.

[0054] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position of substitution is not limited as long as it is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substituents are substituted, the two or more substituents can be the same or different from each other.

[0055] In the present specification, the term "substituted or unsubstituted" means substituted by one, two or more substituents selected from the following: deuterium; nitrile; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted silyl; substituted or unsubstituted aryl; 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, "substituents connected to each other" may include aryl substituted by aryl, aryl substituted by heteroaryl, heterocyclic group substituted by aryl, aryl substituted by alkyl, etc.

[0056] 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 30. 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.

[0057] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and more preferably has 3 to 20 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.

[0058] In the present specification, the aryl group is not particularly limited but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0059] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. 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.

[0060] When the aryl group is a polycyclic aromatic group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specific examples of the polycyclic aromatic group may include naphthyl; anthracenyl; phenanthrenyl; triphenylene; pyrenyl; phenanthene; perylene; fluorenyl; and the like, but are not limited thereto.

[0061] In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0062] When the fluorenyl group is substituted, it may include etc. However, the structure is not limited thereto.

[0063] In the present specification, a heteroaryl group is a group containing one or more atoms that are not 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 heteroaryl group is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group may include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, pyridyl, 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, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl and the like, but are not limited thereto.

[0064] In the present specification, the arylene group has the same definition as the aryl group, except that the arylene group is divalent.

[0065] In the present specification, the heteroarylene group has the same definitions as the heteroaryl group, except that the heteroarylene group is divalent.

[0066] In the present specification, a hydrocarbon ring has the same definitions as an aryl group or a cycloalkyl group, except that the hydrocarbon ring is not monovalent.

[0067] In this specification, Chemical Formula 1 is represented by the following Chemical Formula 1-1.

[0068] [Chemical formula 1-1]

[0069]

[0070] In Chemical Formula 1-1, Ar1, Ar2, X1 and X2 have the same definitions as in Chemical Formula 1.

[0071] In the present specification, the electron blocking layer includes a compound of the following Chemical Formula 1-2 or Chemical Formula 1-3.

[0072] [Chemical formula 1-2]

[0073]

[0074] [Chemical formula 1-3]

[0075]

[0076] In Chemical Formula 1-2 and Chemical Formula 1-3, Ar1, Ar2, X1 and X2 have the same definitions as in Chemical Formula 1.

[0077] In the present specification, the hole transport layer includes a compound of the following Chemical Formula 1-4 or Chemical Formula 1-5.

[0078] [Chemical formula 1-4]

[0079]

[0080] [Chemical formula 1-5]

[0081]

[0082] In Chemical Formula 1-4 and Chemical Formula 1-5, Ar1, Ar2, X1 and X2 have the same definitions as in Chemical Formula 1.

[0083] In this specification, the organic material layer including the compound of Chemical Formula 2 is a light-emitting layer.

[0084] In this specification, Chemical Formula 2 is represented by the following Chemical Formula 2-1 or 2-2.

[0085] [Chemical formula 2-1]

[0086]

[0087] [Chemical formula 2-2]

[0088]

[0089] In chemical formulas 2-1 and 2-2,

[0090] Ar3, R1 and R2, c and d have the same definitions as in Chemical Formula 2.

[0091] In this specification, Chemical Formula 2 is represented by the following Chemical Formula 2-3 or 2-4.

[0092] [Chemical formula 2-3]

[0093]

[0094] [Chemical formula 2-4]

[0095]

[0096] In chemical formulas 2-3 and 2-4,

[0097] Ar3, R1 and R2, c and d have the same definitions as in Chemical Formula 2.

[0098] In the present specification, the organic material layer further includes a light emitting layer, and the triplet energy of the electron blocking layer is greater than the triplet energy of a host of the light emitting layer.

[0099] In the present specification, Ar1 and Ar2 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 heteroaryl group having 2 to 30 carbon atoms.

[0100] In the present specification, Ar1 and Ar2 are independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0101] In the present specification, Ar1 and Ar2 are each a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0102] In the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an unsubstituted or alkyl-substituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0103] In the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0104] In the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an unsubstituted or substituted aryl group having 6 to 30 carbon atoms, which is methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl or hexyl.

[0105] In the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl or triphenylene, and

[0106] The phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl or triphenylene group is unsubstituted or substituted by methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl or hexyl.

[0107] In the present specification, Ar1 and Ar2 are the same as or different from each other and are each independently a phenyl group, a biphenyl group or a fluorenyl group, and

[0108] The phenyl, biphenyl or fluorenyl groups are unsubstituted or substituted by methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl or hexyl groups.

[0109] In the present specification, Ar1 and Ar2 are each independently a phenyl group which is unsubstituted or substituted with one or more substituents selected from methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl and hexyl.

[0110] In the present specification, Ar1 and Ar2 are each independently a biphenyl group which is unsubstituted or substituted with one or more substituents selected from methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl and hexyl.

[0111] In the present specification, Ar1 and Ar2 are each independently a fluorenyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group and a hexyl group.

[0112] In the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a biphenyl group or a fluorenyl group substituted with a methyl group.

[0113] In the present specification, a and b are the same as or different from each other, and are each independently a substituted or unsubstituted aromatic ring having 6 to 10 carbon atoms.

[0114] In the present specification, a and b are a substituted or unsubstituted aromatic ring having 6 to 10 carbon atoms.

[0115] In the present specification, a and b are aromatic rings having 6 to 10 carbon atoms.

[0116] In the present specification, a and b are benzene rings.

[0117] In the present specification, X1 and X2 are the same as or different from each other and are each independently a direct bond or CRR′, and when one of X1 and X2 is a direct bond, the other is CRR′.

[0118] In this specification, X1 is CRR' and X2 is a direct bond.

[0119] In this specification, X1 is CRR' and X2 is CRR'.

[0120] In this specification, X2 is CRR' and X1 is a direct bond.

[0121] In the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0122] In the present specification, Ar3 is an aryl group having 6 to 30 carbon atoms.

[0123] In the present specification, Ar3 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a dibenzothienyl group or a dibenzofuranyl group.

[0124] In the present specification, Ar3 is a phenyl group, a naphthyl group or a dibenzofuranyl group.

[0125] In the present specification, Ar3 is a phenyl group.

[0126] In the present specification, Ar3 is a naphthyl group.

[0127] In the present specification, Ar3 is a dibenzofuranyl group.

[0128] In the present specification, L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0129] In the present specification, L is an arylene group having 6 to 30 carbon atoms.

[0130] In the present specification, L is a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a divalent anthracene group, a divalent phenanthryl group, a divalent fluorenyl group, or a divalent triphenylene group.

[0131] In the present specification, L is a phenylene group, a naphthylene group or a divalent anthracene group.

[0132] In the present specification, L is a phenylene group.

[0133] In the present specification, L is a naphthylene group.

[0134] In the present specification, L is a divalent anthracene group.

[0135] In the present specification, R, R', R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or bond with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring.

[0136] In the present specification, R, R', R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group, or bond with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring.

[0137] In the present specification, R, R', R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0138] In the present specification, R, R', R1 and R2 are hydrogen or deuterium, or bond with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring.

[0139] In the present specification, R, R', R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, or an unsubstituted or alkyl-substituted aryl group, or bond with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring.

[0140] In the present specification, R, R', R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, or an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, or is bonded to an adjacent substituent to form a hydrocarbon ring which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

[0141] In the present specification, R, R', R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, or an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with a methyl, ethyl, propyl, isopropyl, butyl or tert-butyl group, or is bonded to an adjacent substituent to form a hydrocarbon ring which is unsubstituted or substituted with a methyl, ethyl, propyl, isopropyl, butyl or tert-butyl group.

[0142] In the present specification, R, R', R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, phenyl or biphenyl, and

[0143] The phenyl or biphenyl group may be unsubstituted or substituted with methyl, ethyl, propyl, isopropyl, butyl or tert-butyl.

[0144] In the present specification, the compound of Chemical Formula 1 may be selected from the following specific examples.

[0145]

[0146]

[0147]

[0148]

[0149] In one embodiment of the present disclosure, the compound of Chemical Formula 2 is any one of the following structural formulas.

[0150]

[0151]

[0152]

[0153] In the organic light emitting device of the present disclosure, the organic material layer includes an electron blocking layer and a light emitting layer, and the triplet energy of the electron blocking layer is greater than the triplet energy of a host of the light emitting layer.

[0154] In order to improve the fluorescence luminescence efficiency, triplet-triplet annihilation needs to occur actively in the light-emitting layer. To this end, the triplet energy of the light-emitting layer needs to be low to separate the triplet excitons in the light-emitting layer, and on the other hand, the triplet energy of the electron blocking layer needs to be high to prevent the triplet energy of the light-emitting layer from being transferred to other layers.

[0155] In the specification of the present disclosure, the organic material layer includes one or more light emitting layers.

[0156] In the specification of the present disclosure, the organic material layer includes a light-emitting layer, and contains anthracene and terminal naphthalene as the main body of the light-emitting layer, and when the carbon in anthracene connected to naphthalene is referred to as CA and the carbon in naphthalene connected to anthracene is referred to as CB, the distance between CA and CB is greater than or equal to and less than or equal to

[0157] In the description of the present disclosure, the distance between CA and CB is greater than or equal to and less than or equal to

[0158] In the description of the present disclosure, the distance between CA and CB is greater than or equal to and less than or equal to

[0159] When the distance between carbon-carbon (CA and CB) is kept greater than or equal to and less than or equal to When the anthracenes are accumulated by extending the molecule, the distance between them can be kept close, which is beneficial for charge transfer.

[0160] In the specification of the present disclosure, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Chemical Formula 2 as a host of the light emitting layer.

[0161] For example, the organic light-emitting device of the present disclosure may have Figure 1 The structure shown in , however, the structure is not limited thereto.

[0162] Figure 1 The structure of an organic light-emitting device is shown in which a first electrode 2, an organic material layer 3 and a second electrode 4 are sequentially laminated on a substrate 1. The organic material layer 3 includes a hole transport layer, an electron blocking layer and a light-emitting layer, and may include another organic material layer between the hole transport layer and the electron blocking layer and between the electron blocking layer and the light-emitting layer.

[0163] Figure 1 An organic light emitting device is shown, however, the structure is not limited thereto.

[0164] Figure 2The structure of an organic light-emitting device in which a first electrode 2, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8 and a second electrode 4 are sequentially laminated on a substrate 1 is shown. Figure 2 Additional layers of organic materials are included between the various layers.

[0165] Figure 3 The structure of an organic light-emitting device is shown in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, an electron transport layer 9, an electron injection layer 10 and a second electrode 4 are sequentially laminated on a substrate 1.

[0166] Figure 3 An organic light emitting device is shown, however, the structure is not limited thereto.

[0167] In the specification of the present disclosure, the organic material layer may further include a hole injection layer, a hole transport layer, or a hole injection and transport layer.

[0168] In the specification of the present disclosure, the organic material layer may further include an electron injection layer, an electron transport layer, or an electron injection and transport layer.

[0169] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a dual emission type according to the materials used.

[0170] Embodiments of the invention

[0171] The organic light-emitting device of the present disclosure may be manufactured using common organic light-emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-mentioned compounds.

[0172] [Preparation Example of Chemical Formula 1]

[0173]

[0174] In the preparation examples, Ar1, Ar2, X1, X2, a and b have the same definitions as in Chemical Formula 1, and X is a halogen atom.

[0175] [Preparation Example of Chemical Formula 2]

[0176]

[0177] In the preparation example of Chemical Formula 2, L and Ar3 have the same definitions as in Chemical Formula 2.

[0178] The preparation examples and the following synthesis examples are intended to illustrate the present disclosure to those skilled in the art, but the present disclosure is not limited thereto. All compounds described in the present disclosure may be prepared by changing the starting materials, intermediates, and the types and positions of substituents in the preparation examples and the following synthesis examples.

[0179] [Synthesis example]

[0180] Synthesis Example 1: Synthesis of HT-1

[0181]

[0182] After intermediate A-1 (12.0 g, 30.4 mmol) and intermediate B-1 (12.1 g, 33.4 mmol) were dissolved in xylene (300 ml), sodium tert-butoxide (8.8 g, 91.1 mmol) and Pd(P(t-Bu)3)2 (0.3 g, 0.6 mmol) were introduced therein, and the resultant was stirred for 6 hours under argon atmosphere and reflux conditions. When the reaction was completed, the resultant was cooled to room temperature, and after water was introduced therein, the reaction solution was transferred to a separatory funnel and extracted. The extracted solution was dried over MgSO4, filtered and concentrated, and after the sample was purified using silica gel column chromatography, HT-1 (7.2 g) was obtained by sublimation purification. (yield 35%, MS [M + H] + =675)

[0183] Synthesis Example 2: Synthesis of HT-2

[0184]

[0185] HT-2 was prepared in the same manner as for the preparation of HT-1, except that the intermediate A-1 in Synthesis Example 1 was changed to intermediate A-2, and the intermediate B-1 was changed to intermediate B-2. (MS [M + H] + =717)

[0186] Synthesis Example 3: Synthesis of HT-3

[0187]

[0188] HT-3 was prepared in the same manner as for the method for preparing HT-1, except that the intermediate A-1 in Synthesis Example 1 was changed to intermediate A-3, and the intermediate B-1 was changed to intermediate B-3. (MS [M + H] + =748)

[0189] Synthesis Example 4: Synthesis of HT-4

[0190]

[0191] HT-4 was prepared in the same manner as for the preparation of HT-1, except that the intermediate A-1 in Synthesis Example 1 was changed to intermediate A-3. (MS [M+H] + =788)

[0192] Synthesis Example 5: Synthesis of EB-1

[0193]

[0194] EB-1 was prepared in the same manner as for the preparation of HT-1, except that the intermediate A-1 in Synthesis Example 1 was changed to intermediate A-4, and the intermediate B-1 was changed to intermediate B-4. (MS [M + H] + =637)

[0195] Synthesis Example 6: Synthesis of EB-2

[0196]

[0197] EB-2 was prepared in the same manner as for the preparation of HT-1, except that the intermediate A-1 in Synthesis Example 1 was changed to intermediate A-5, and the intermediate B-1 was changed to intermediate B-5. (MS [M + H] + =675)

[0198] Synthesis Example 7: Synthesis of EB-3

[0199]

[0200] EB-3 was prepared in the same manner as that used to prepare HT-1, except that the intermediate A-1 in Synthesis Example 1 was changed to intermediate A-6, and the intermediate B-1 was changed to intermediate B-2. (MS [M+H] + =717)

[0201] Synthesis Example 8: Synthesis of EB-4

[0202]

[0203] EB-4 was prepared in the same manner as for the preparation of HT-1, except that the intermediate A-1 in Synthesis Example 1 was changed to intermediate A-7, and the intermediate B-1 was changed to intermediate B-4. (MS [M + H] + =635)

[0204] Synthesis Example 9: Synthesis of BH-1

[0205] Step 1) Synthesis of intermediate C-1

[0206]

[0207] After 9-bromoanthracene (20.0 g, 77.8 mmol) and (4-(naphthalene-1-yl)phenyl)boric acid (21.2 g, 85.6 mmol) were dissolved in THF (300 ml), K2CO3 (43.0 g, 311.1 mmol) dissolved in H2O (150 ml) was introduced thereto. Pd(PPh3)4 (3.6 g, 3.1 mmol) was introduced thereto, and the resultant was stirred for 8 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the resultant was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with water and ethyl acetate. The extracted solution was dried over MgSO4, filtered and concentrated, and after the sample was purified using silica gel column chromatography, intermediate C-1 (21.6 g) was obtained. (Yield 73%, MS [M+H] + =380)

[0208] Step 2) Synthesis of intermediate C-2

[0209]

[0210] After introducing intermediate C-1 (20.0 g, 52.6 mmol), NBS (9.8 g, 55.2 mmol) and DMF (400 ml), the resultant was stirred at room temperature for 8 hours under argon atmosphere. After the reaction was completed, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extracted solution was dried, filtered and concentrated with MgSO4, and after the sample was purified by silica gel column chromatography, intermediate C-2 (21.0 g) was obtained. (yield 87%, MS [M + H] + =459)

[0211] Step 3) Synthesis of BH-1

[0212]

[0213] After intermediate C-2 (15.0 g, 32.7 mmol) and phenylboronic acid (4.4 g, 35.9 mmol) were dissolved in THF (225 ml), K2CO3 (18.1 g, 130.6 mmol) dissolved in H2O (113 ml) was introduced thereto. Pd(PPh3)4 (1.5 g, 1.3 mmol) was introduced thereto, and the resultant was stirred for 8 hours under reflux conditions in an argon atmosphere. When the reaction was complete, the resultant was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with water and ethyl acetate. The extracted solution was dried with MgSO4, filtered and concentrated, and after the sample was purified using silica gel column chromatography, BH-1 (4.8 g) was obtained by sublimation purification. (yield 32%, MS [M + H] + =456)

[0214] Synthesis Example 10: Synthesis of BH-2

[0215]

[0216] BH-2 was prepared in the same manner as that used to prepare BH-1, except that (4-(naphthalen-1-yl)phenyl)boronic acid in Synthesis Example 9 was changed to [1,2'-binaphthyl]-4-ylboronic acid. (MS[M+H] + =506)

[0217] Synthesis Example 11: Synthesis of BH-3

[0218]

[0219] BH-3 was prepared in the same manner as that used to prepare BH-1, except that the phenylboronic acid in step 3 of Synthesis Example 9 was changed to dibenzo[b,d]furan-2-ylboronic acid. (MS[M+H] + =546)

[0220] [Example]

[0221] Example 1

[0222] It is coated with a thickness of Indium tin oxide (ITO) of 1000nm is put into the distilled water dissolved with detergent and carries out ultrasonic cleaning as the glass substrate of film.Here, the product of Fischer Co. is used as detergent, and the distilled water filtered twice by the filter manufactured by Millipore Co. is used as distilled water.After ITO is cleaned for 30 minutes, distilled water is used to repeat ultrasonic cleaning twice and continues for 10 minutes.After finishing with distilled water cleaning, the solvent of substrate isopropanol, acetone and methanol is carried out ultrasonic cleaning, then dried, and then transferred to plasma cleaner.In addition, substrate is cleaned for 5 minutes using oxygen plasma, and then transferred to vacuum deposition device.

[0223] On the transparent ITO electrode prepared as above, the following HT-1 and PD were thermally vacuum deposited at a weight ratio of 95:5. The hole injection layer is then formed by depositing only the HT-1 material to a thickness of The hole transport layer was formed by thermal vacuum deposition of the compound represented by the following EB-1 to a thickness of Subsequently, the following compounds represented by BH-1 and BD were vacuum deposited onto the substrate at a weight ratio of 96:4. Subsequently, the compound represented by the following ET and Liq was thermally vacuum deposited onto the The thickness of the electron transport layer is then vacuum deposited on the electron transport layer to On the electron injection layer, magnesium and silver were sequentially deposited in a weight ratio of 10:1 to form an electron injection layer. and deposit aluminum to The cathode is formed with a thickness of , and as a result, an organic light emitting device is manufactured.

[0224]

[0225] Examples 2 to 16 and Comparative Examples 1 to 13

[0226] An organic light emitting device was manufactured in the same manner as in Example 1, except that the compounds described in Table 1 below were used instead of the hole transport layer material, the electron blocking layer material, and the host material in Example 1.

[0227]

[0228] For each organic light-emitting device manufactured in the embodiment and the comparative example, the current when 10 mA / cm 2 The device performance at current density of 20 mA / cm 2 The time taken for the initial brightness to decrease to 90% at the current density of 1.34° is shown in Table 1.

[0229] [Table 1]

[0230]

[0231] For the hole transport layer materials, electron blocking layer materials and light emitting layer host materials used in the embodiments and comparative examples, the triplet energy was calculated by quantum calculation, and the results are shown in Table 2. As quantum calculation, the structure was optimized by density functional theory (DFT) of Schrodinger Material Science Suite program, and then the triplet energy was calculated by time dependent density functional theory (TD-DFT). Here, B3LYP was used as a function, and 6-31G* was used as a basis function.

[0232] [Table 2]

[0233] Material T1(eV) HT-1 2.62 HT-2 2.58 HT-3 2.66 HT-4 2.83 HT-A 2.80 EB-1 2.82 EB-2 2.70 EB-3 2.69 EB-4 2.86 EB-A 1.69 BH-1 1.73 BH-2 1.73 BH-3 1.73 BH-A 1.73

[0234] When Comparative Examples 1 to 7, Examples 7 and 8, and the like are compared, it can be seen that a sufficient long-life effect can be obtained only by using the compound of the present disclosure in each of the hole transport layer, the electron blocking layer, and the light-emitting layer.

[0235] When the compound represented by Chemical Formula 1 of the present disclosure is used in the hole transport layer and the electron blocking layer, due to the similar structure, characteristics that are conducive to hole injection and migration can be obtained. In particular, when the compound is used in each of the layers while changing the substitution position of the amine group, the characteristics can be controlled to be suitable for the role of each layer. When Comparative Examples 10 and 11 are compared with Examples 4 and 7, it can be seen that when different compounds are used, a significantly long life is obtained compared to when the same compound is used in the hole transport layer and the electron blocking layer.

[0236] Furthermore, when the structure of Chemical Formula 2 is used as a host material, the angle between anthracene of Chemical Formula 2 and L is perpendicular, the conjugation length can be controlled to be short and the distance between anthracenes accumulated by extending the molecule can be kept close, which is beneficial to charge transfer.

[0237] In the fused aryl group, as the number of fused rings increases, the triplet energy decreases. Since the structure of Chemical Formula 2 used as the host of the light-emitting layer includes an anthracene structure, when the structure of Chemical Formula 1 includes a functional group containing three or more 6-membered rings such as anthracene, the triplet energy may be smaller than that of the light-emitting layer host.

[0238] Therefore, in Comparative Examples 2 to 5 using EB-A, the triplet energy of the material used in the layer in contact with the light-emitting layer becomes smaller than the triplet energy of the main material of the light-emitting layer, and since it cannot act as a blocking layer, the charges are outside the light-emitting layer, and thus the lifetime is reduced.

[0239] Even when the structure of Chemical Formula 1 is maintained, the material used as the electron blocking layer needs to have a triplet energy greater than the main material of the light-emitting layer to function as a blocking layer. Compared with other materials, EB-A of Table 2 has a smaller triplet energy, and in particular, has a triplet energy even smaller than the main material, and it can be seen that since it cannot function as a blocking layer in this case, the device efficiency is reduced. When such a result is considered, the organic electroluminescent device that meets the conditions of the present disclosure can obtain the characteristics of low voltage, high efficiency and long life.

[0240] The materials having two amine groups used in Comparative Examples 12 and 13, such as HT-B, have an increased HOMO energy level compared to the structure of Chemical Formula 1 due to the addition of an amine group that acts as an electron donor. When the material is used in the hole transport layer as in Comparative Example 12, a low driving voltage is obtained because there is no problem in hole injection, however, there is excessive hole injection in the light-emitting layer due to the movement of the light-emitting region in the direction of the electron transport layer, resulting in reduced efficiency. At the same time, when HT-B is used in the electron blocking layer as in Comparative Example 13, it can be seen that the difference in HOMO energy level between the electron blocking layer and the light-emitting layer increases, thereby preventing hole injection into the light-emitting layer, and therefore, the overall device characteristics are reduced.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and an organic material layer disposed between the first electrode and the second electrode, The organic material layer includes a hole transport layer and an electron blocking layer, and the electron blocking layer includes a compound of the following Chemical Formula 1-2 or Chemical Formula 1-3: The hole transport layer comprises a compound of the following Chemical Formula 1-4 or Chemical Formula 1-5; One or more layers of the organic material layer that are neither the hole transport layer nor the electron blocking layer include a compound of the following Chemical Formula 2: [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical formula 1-5] In Chemical Formulas 1-2 to 1-5, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a biphenyl group which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, or a fluorenyl group which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; X1 and X2 are the same as or different from each other and are each independently a direct bond or CRR'; and When one of X1 and X2 is a direct bond, the other is CRR'; R and R' are the same as or different from each other and are each independently an unsubstituted phenyl group, or bonded with an adjacent substituent to form a fluorene ring which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, [Chemical formula 2] In chemical formula 2, Ar3 is phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, dibenzothienyl or dibenzofuranyl; L is phenylene, naphthylene or divalent anthracene; R1 and R2 are hydrogen; c is 8; d is 7. 2 . The organic light emitting device according to claim 1 , wherein the organic material layer comprising the compound of Chemical Formula 2 is a light emitting layer.

3. The organic light-emitting device according to claim 2, wherein Chemical Formula 2 is represented by the following Chemical Formula 2-1 or 2-2: [Chemical formula 2-1] [Chemical formula 2-2] In chemical formulas 2-1 and 2-2, Ar3, R1 and R2, c and d have the same definitions as in Chemical Formula 2.

4. The organic light-emitting device according to claim 2, wherein Chemical Formula 2 is represented by the following Chemical Formula 2-3 or 2-4: [Chemical formula 2-3] [Chemical formula 2-4] In chemical formulas 2-3 and 2-4, Ar3, R1 and R2, c and d have the same definitions as in Chemical Formula 2. 5 . The organic light emitting device according to claim 1 , wherein the organic material layer comprises a light emitting layer, and the triplet energy of the electron blocking layer is greater than the triplet energy of a host of the light emitting layer.

6. The organic light-emitting device according to claim 1, wherein Chemical Formula 1-2 or Chemical Formula 1-3 is any one of the following compounds:

7. The organic light-emitting device according to claim 1, wherein Chemical Formula 1-4 or Chemical Formula 1-5 is any one of the following compounds:

8. The organic light-emitting device according to claim 1, wherein Chemical Formula 2 is any one of the following compounds:

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