Organic Light Emitting Diodes

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 one, two or more organic material layers arranged between the first electrode and the second electrode, wherein the organic material layers include a first organic material layer including a compound of Chemical Formula 1 and a second organic material layer including a compound of Chemical Formula 2.

Description

Technical Field

[0001] This disclosure claims priority to and the benefit of Korean Patent Application No. 10-2019-0004682, filed on January 14, 2019, 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, 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 from the anode and the cathode into the organic material layer, respectively, and excitons are formed when the injected holes and electrons meet, 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, which includes a first electrode; a second electrode arranged opposite to the first electrode; and one, two or more organic material layers arranged between the first electrode and the second electrode, wherein the organic material layers include a first organic material layer including a compound of the following Chemical Formula 1 and a second organic material layer including a compound of the following Chemical Formula 2.

[0009] [Chemical formula 1]

[0010]

[0011] [Chemical formula 2]

[0012]

[0013] In Chemical Formulas 1 and 2,

[0014] Ar1 to Ar4 are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heteroaryl group,

[0015] R1 is hydrogen, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, an aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heteroaryl group,

[0016] R2 to R8 are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heteroaryl group,

[0017] L1 to L7 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0018] p1, q1, r1, s1, p2, q2 and r2 are each an integer from 0 to 2,

[0019] When p1, q1, r1, s1, p2, q2 and r2 are 2, the substituents in the brackets are the same or different from each other,

[0020] a and e to h are integers from 0 to 4,

[0021] b is an integer from 0 to 3,

[0022] c and d are integers from 0 to 2,

[0023] d+f≤5,

[0024] c+g≤5, and

[0025] When c and d are 2, the substituents in the brackets are the same or different from each other,

[0026] When a, b, e, f are 2 or more, the substituents in the brackets are the same as or different from each other.

[0027] Beneficial Effects

[0028] By using the compound represented by Chemical Formula 1 as a hole transport layer and using the compound represented by Chemical Formula 2 as an electron blocking layer, the organic light emitting device according to one embodiment of the present specification can control the HOMO energy level and LUMO energy level of the compound, thereby controlling the energy barrier of each organic material layer. In this way, the effects of low voltage, high efficiency and long life can be obtained in the organic light emitting device according to one embodiment of the present specification. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1 An organic light emitting device according to one embodiment of the present specification is shown.

[0030] Figure 2 An organic light emitting device according to one embodiment of the present specification is shown.

[0031] [reference numerals]

[0032] 1: Base

[0033] 2: First electrode

[0034] 3: Hole transport layer

[0035] 4: Electron blocking layer

[0036] 5: Luminous layer

[0037] 6: Second electrode

[0038] 7: Hole injection layer

[0039] 8: Hole blocking layer

[0040] 9: Electron injection and transport layer DETAILED DESCRIPTION

[0041] Hereinafter, the present specification will be described in more detail.

[0042] One embodiment of the present specification provides an organic light-emitting device, which includes a first electrode; a second electrode arranged opposite to the first electrode; and one, two or more organic material layers arranged between the first electrode and the second electrode, wherein the organic material layers include a first organic material layer including a compound of Chemical Formula 1 and a second organic material layer including a compound of Chemical Formula 2.

[0043] 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.

[0044] 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.

[0045] Examples of the substituent in the present specification are described below, however, the substituent is not limited thereto.

[0046] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed into 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 identical or different from each other.

[0047] 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 exemplified 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.

[0048] 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, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0049] 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; and the like, but are not limited thereto.

[0050] 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.

[0051] 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.

[0052] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specific examples of the polycyclic aryl group may include naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, phenanthrenyl, perylene, fluorenyl, etc., but are not limited thereto.

[0053] In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0054] When the fluorenyl group is substituted, it may include etc. However, the structure is not limited thereto.

[0055] In the present specification, a heteroaryl group is a group containing one or more non-carbon atoms (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 heterocyclic groups 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.

[0056] In the present specification, the arylene group has the same definition as the aryl group, except that the arylene group is divalent.

[0057] In the present specification, the heteroarylene group has the same definitions as the heteroaryl group, except that the heteroarylene group is divalent.

[0058] 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.

[0059] In the present specification, R2 to R8 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or silyl group substituted with an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, an arylalkyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

[0060] In the present specification, R2 to R8 are the same as or different from each other, and are each independently hydrogen; deuterium; an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with an arylalkyl group having 6 to 30 carbon atoms or an alkyl group having 1 to 10 carbon atoms; or a heteroaryl group having 3 to 30 carbon atoms.

[0061] In the present specification, R2 to R8 are the same as or different from each other and are each independently hydrogen; deuterium; phenyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; naphthyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; biphenyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; terphenyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; anthracenyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; phenanthryl; triphenylene which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; fluorenyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms or an alkyl group having 1 to 10 carbon atoms; spirobifluorenyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; carbazolyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; dibenzofuranyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; or dibenzothiophenyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms.

[0062] In the present specification, R2 to R8 are the same as or different from each other and are each independently hydrogen; deuterium; phenyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; biphenyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; naphthyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; terphenyl; quaterphenyl; phenanthrenyl; triphenylene; spirobifluorenyl; fluorenyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms or an alkyl group having 1 to 10 carbon atoms; carbazolyl which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; dibenzofuranyl; or dibenzothiophenyl.

[0063] In the present specification, R2 to R8 are the same as or different from each other, and are each independently any one selected from the following chemical formulae.

[0064]

[0065] Dashed lines indicate bonding to the core.

[0066] Rx are the same as or different from each other, and are each deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0067] In the present specification, R2 is hydrogen.

[0068] In the present specification, R3 to R8 are the same as or different from each other, and are each independently hydrogen, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0069] In the present specification, R3 to R8 are the same as or different from each other, and are each independently hydrogen, 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, a phenyl group which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms, a biphenyl group which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms, or a naphthyl group which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms.

[0070] In the present specification, R3 to R8 are the same as or different from each other, and are each independently hydrogen, phenyl, biphenyl or naphthyl.

[0071] In the present specification, R3 to R8 are the same as or different from each other, and are each independently hydrogen or phenyl.

[0072] In the present specification, R1 is hydrogen, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group, an aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0073] In the present specification, R1 is hydrogen; an aryl group having 6 to 30 carbon atoms; or a heteroaryl group having 3 to 30 carbon atoms.

[0074] In the present specification, R1 is hydrogen; an aryl group having 6 to 20 carbon atoms; or a heteroaryl group having 3 to 20 carbon atoms.

[0075] In the present specification, R1 is hydrogen; an aryl group having 6 to 15 carbon atoms; or a heteroaryl group having 3 to 15 carbon atoms.

[0076] In the present specification, R1 is hydrogen.

[0077] In the present specification, when R1 is hydrogen, the effects of low voltage, high efficiency and long life are obtained compared with when substituted with other substituents such as deuterium or a substituted aryl group.

[0078] In the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkenyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0079] In the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylalkenyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0080] In the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0081] In the present specification, Ar1 is phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthryl, triphenylene, fluorenyl or pyrenyl, and

[0082] The phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl or pyrenyl groups are unsubstituted or substituted with deuterium, a nitrile group, a halogen group, an amine group, a silyl group, a phosphine oxide group, an alkyl group, an aryl group or a heteroaryl group.

[0083] In the present specification, Ar1 is a phenyl group, a naphthyl group or a biphenyl group, and the phenyl group, the naphthyl group or the biphenyl group is unsubstituted or substituted with a deuterium group, a nitrile group, a halogen group, an amine group, a silyl group, a phosphine oxide group, an alkyl group, an aryl group or a heteroaryl group.

[0084] In the present specification, Ar1 is a phenyl group, a naphthyl group or a biphenyl group, and the phenyl group, the naphthyl group or the biphenyl group is unsubstituted or substituted with deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms.

[0085] In the present specification, Ar1 is phenyl, naphthyl or biphenyl, and phenyl, naphthyl or biphenyl is unsubstituted or substituted by deuterium, a halogen group, methyl, ethyl, propyl, butyl, pentyl, phenyl, naphthyl, biphenyl, anthracenyl, tert-butyl or carbazolyl.

[0086] In the present specification, Ar1 is a phenyl group, a naphthyl group or a biphenyl group.

[0087] In the present specification, Ar2 and Ar3 are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, 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.

[0088] In the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, 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.

[0089] In the present specification, Ar2 and Ar3 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 3 to 30 carbon atoms.

[0090] In the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0091] In the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms.

[0092] In the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, spirobifluorenyl or pyrenyl, and

[0093] The phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, spirobifluorenyl or pyrenyl groups are unsubstituted or substituted with deuterium, a nitrile group, a halogen group, an amine group, a silyl group, a phosphine oxide group, an alkyl group, an aryl group or a heteroaryl group.

[0094] In the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, fluorenyl or spirobifluorenyl, and

[0095] The phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, fluorenyl or spirobifluorenyl groups are unsubstituted or substituted with deuterium, a nitrile group, a halogen group, an amine group, a silyl group, a phosphine oxide group, an alkyl group, an aryl group or a heteroaryl group.

[0096] In the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, fluorenyl or spirobifluorenyl, and

[0097] Phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, fluorenyl or spirobifluorenyl is unsubstituted or substituted by deuterium, a halogen group, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a naphthyl group, a biphenyl group, an anthracenyl group, a tert-butyl group or a carbazolyl group.

[0098] In the present specification, Ar2 and Ar3 are the same as or different from each other and are each independently a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group, and the carbazolyl group, the dibenzofuranyl group or the dibenzothiophenyl group is unsubstituted or substituted by: a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group or a naphthyl group.

[0099] In the present specification, Ar2 and Ar3 are the same as or different from each other and are each independently phenyl, naphthyl, biphenyl, terphenyl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, phenanthrenyl, spirobifluorenyl, unsubstituted or phenyl-substituted carbazolyl, dibenzofuranyl, or dibenzothiophenyl.

[0100] In the present specification, Ar4 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, 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.

[0101] In the present specification, Ar4 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.

[0102] In the present specification, Ar4 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0103] In the present specification, Ar4 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms.

[0104] In the present specification, Ar4 is phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, spirobifluorenyl or pyrenyl, and

[0105] The phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, spirobifluorenyl or pyrenyl groups are unsubstituted or substituted with deuterium, a nitrile group, a halogen group, an amine group, a silyl group, a phosphine oxide group, an alkyl group, an aryl group or a heteroaryl group.

[0106] In the present specification, Ar4 is phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, pyrenyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl, and

[0107] Phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, pyrenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl is unsubstituted or substituted with deuterium, nitrile, phenyl, biphenyl, naphthyl, methyl, ethyl, or tert-butyl.

[0108] In the present specification, Ar4 is a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group, and the carbazolyl group, the dibenzofuranyl group or the dibenzothiophenyl group is unsubstituted or substituted by a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group or a naphthyl group.

[0109] In the present specification, Ar4 is an unsubstituted or deuterium-substituted phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthryl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, pyrene, an unsubstituted or phenyl-substituted carbazolyl, an unsubstituted or phenyl-substituted dibenzofuranyl, or an unsubstituted or phenyl-substituted dibenzothiophenyl group.

[0110] In the present specification, L1 to L7 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

[0111] In the present specification, L1 to L7 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

[0112] In the present specification, L1 to L7 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 15 carbon atoms.

[0113] In the present specification, L1 to L7 are the same as or different from each other and are each independently a direct bond; an unsubstituted or deuterium, alkyl or aryl-substituted arylene group having 6 to 30 carbon atoms; or an unsubstituted or aryl-substituted heteroarylene group containing any one or more of N, O and S having 3 to 30 carbon atoms.

[0114] In the present specification, L1 to L7 are the same as or different from each other, and are each independently a direct bond, an unsubstituted or deuterium-substituted phenylene group, an unsubstituted or deuterium-substituted biphenylene group, an unsubstituted or deuterium-substituted terphenylene group, an unsubstituted or deuterium-substituted naphthylene group, a divalent fluorenyl group substituted with an alkyl group or an aryl group, a divalent carbazolyl group unsubstituted or aryl group-substituted, a divalent dibenzofuranyl group, or a divalent dibenzothiophenyl group.

[0115] In the present specification, L1 to L7 are the same as or different from each other, and are each independently any one selected from the following substituents.

[0116] R 16 and R 17 are the same as or different from each other, and are each deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0117] In the present specification, L1 to L4 are the same as or different from each other, and are each independently a direct bond, a phenylene group, a biphenylene group, a naphthylene group, or a divalent carbazolyl group.

[0118] In the present specification, L5 to L7 are the same as or different from each other, and are each independently a phenylene group, a naphthylene group, a divalent biphenyl group or a divalent carbazole group, and

[0119] The phenylene group, naphthylene group, divalent biphenyl group or divalent carbazolyl group is unsubstituted or substituted with deuterium, a nitrile group, a halogen group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group or a naphthyl group.

[0120] In the present specification, L5 to L7 are the same as or different from each other, and are each independently a naphthylene group, a divalent carbazolyl group or a divalent biphenyl group, or an unsubstituted or deuterium-substituted phenylene group.

[0121] In the present specification, the compound of Chemical Formula 1 may be selected from the following specific examples.

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130] In one embodiment of the present disclosure, the compound of Chemical Formula 2 is any one of the following structural formulas.

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150] In the specification of the present disclosure, the first organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound of Chemical Formula 1.

[0151] In the specification of the present disclosure, the first organic material layer includes a hole transport layer, and the hole transport layer includes the compound of Chemical Formula 1.

[0152] In the organic light emitting device of the present disclosure, the second organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound of Chemical Formula 2.

[0153] In the specification of the present disclosure, the organic material layer includes one or more light emitting layers.

[0154] In the specification of the present disclosure, the organic material layer includes a light emitting layer.

[0155] For example, the organic light-emitting device of the present disclosure may have Figure 1 and Figure 2 The structure shown in , however, the structure is not limited thereto.

[0156] Figure 1 The structure of an organic light-emitting device in which a first electrode 2 , a hole transport layer 3 , an electron blocking layer 4 , a light-emitting layer 5 , and a second electrode 6 are sequentially laminated on a substrate 1 is shown.

[0157] Figure 2 The structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 7, a hole transport layer 3, an electron blocking layer 4, a light-emitting layer 5, a hole blocking layer 8, an electron injection and transport layer 9 and a second electrode 6 are sequentially laminated on a substrate 1 is shown.

[0158] In the specification of the present disclosure, the organic light emitting device includes a structure in which a second electrode / a light emitting layer / an electron blocking layer / a hole transport layer / a first electrode are sequentially layered.

[0159] In the specification of the present disclosure, the organic light emitting device includes a structure in which a second electrode / electron transport layer / light emitting layer / electron blocking layer / hole transport layer / first electrode are sequentially layered.

[0160] In the specification of the present disclosure, the organic light emitting device includes a structure in which a second electrode / electron transport layer / light emitting layer / electron blocking layer / hole transport layer / hole injection layer / first electrode are sequentially layered.

[0161] In the specification of the present disclosure, the organic light emitting device includes a structure in which a second electrode / a light emitting layer / an electron blocking layer / a hole transport layer / a hole injection layer / a first electrode are sequentially layered.

[0162] In the specification of the present disclosure, the organic light emitting device includes a structure in which a second electrode / electron injection layer / electron transport layer / light emitting layer / electron blocking layer / hole transport layer / first electrode are sequentially layered.

[0163] In the specification of the present disclosure, the organic light emitting device includes a structure in which a second electrode / electron injection layer / electron transport layer / light emitting layer / electron blocking layer / hole transport layer / hole injection layer / first electrode are sequentially layered.

[0164] In the specification of the present disclosure, the organic light-emitting device includes a structure in which second electrode / electron injection layer / electron transport layer / hole blocking layer / light-emitting layer / electron blocking layer / hole transport layer / hole injection layer / first electrode are sequentially stacked.

[0165] The organic light-emitting device of the present specification may be manufactured using materials and methods known in the art, except that the compound of Chemical Formula 1 is used to form the hole transport layer and the compound of Chemical Formula 2 is used to form the electron blocking layer.

[0166] For example, the organic light-emitting device according to the present disclosure can be manufactured by forming an anode on a substrate by depositing a metal, a conductive metal oxide, or an alloy thereof using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation; forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode, a first organic material layer containing a compound of Chemical Formula 1, and a second organic material layer containing a compound of Chemical Formula 2; and then depositing a material that can be used as a cathode thereon. In addition to such a method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0167] As the anode material, a material with a large work function is generally preferred so that holes are smoothly injected into the organic material layer. Specific examples of anode materials that can be used in the present disclosure include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but are not limited thereto.

[0168] As the cathode material, a material having a small work function is generally preferred so that electrons can be smoothly injected into the organic material layer. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; etc., but are not limited thereto.

[0169] The hole injection material is a material that can advantageously receive holes from the anode at a low voltage, and 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, etc., but are not limited thereto.

[0170] The light-emitting 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-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based azoles, benzothiazole-based and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene; and the like, but are not limited thereto.

[0171] The light-emitting layer may include a host material and a dopant material. The host material may include a fused aromatic ring derivative, a heterocyclic compound, and the like. Specifically, as a fused aromatic ring derivative, anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like may be included, and as a heterocyclic compound, a heterocyclic compound, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, and the like may be included, however, the host material is not limited thereto.

[0172] The dopant material may include aromatic heterocyclic compounds, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic heterocyclic compound is a fused aromatic ring derivative having a substituted or unsubstituted arylamino group, and may include pyrene, anthracene, Diindenopyrene (peryflanthene) and the like. As the styrylamine compound, a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group can be used, and one, two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino groups are substituted or unsubstituted. Specifically, styrylamine, styrene diamine, styrene triamine, styrene tetramine and the like can be included, however, the styrylamine compound is not limited thereto. In addition, as the metal complex, an iridium complex, a platinum complex and the like can be included, however, the metal complex is not limited thereto.

[0173] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and as an electron transport material, such a material is suitable: it can advantageously receive electrons from the cathode, move the electrons to the light-emitting layer, and has a high electron mobility. Specific examples thereof include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes; and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials may include commonly used materials having a low work function and followed by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium are included, and in each case followed by an aluminum layer or a silver layer.

[0174] The electron injection layer is a layer that injects electrons from the electrode, and preferably a compound that has an electron transporting ability, 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, and 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, tetracarboxylic acid, fluorenyl methane, anthrone and the like and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives and the like, but not limited thereto.

[0175] 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.

[0176] The hole blocking layer is a layer that blocks holes from reaching the cathode and can generally be formed under the same conditions as the hole injection layer. Specific examples thereof may include Oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but not limited thereto.

[0177] The organic light emitting device of the present disclosure may be manufactured using a common organic light emitting device manufacturing method and materials, except that an organic material layer including a hole transport layer using the compound of Chemical Formula 1 above and an electron blocking layer using the compound of Chemical Formula 2 above is formed.

[0178] Embodiments of the invention

[0179] Synthesis Example 1. Synthesis of Compound 1-1

[0180]

[0181] After toluene (200 ml) was added to 3-(4-bromophenyl)-9-phenyl-9H-carbazole (20.0 g, 50.21 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1',4',1″-terphenyl]-4-amine (20.36 g, 51.22 mmol) and sodium tert-butoxide (6.76 g, 70.29 mmol), the resultant was stirred while heating for 10 minutes. To the mixture was added bis(tri-tert-butylphosphine)palladium (BTP, 0.08 g, 0.15 mmol) dissolved in toluene (10 ml), and the resultant was stirred while heating for 1 hour. After terminating the reaction and filtering the resultant, the layers were separated using toluene and water. After removing the solvent, the resultant was recrystallized with ethyl acetate to obtain compound 1-1 (29.5 g, 82.18% yield). (MS[M+H]+=715)

[0182] Synthesis Example 2. Synthesis of Compound 1-2

[0183] Compound 1-2 (27.5 g, 80.68% yield) was obtained in the same manner as in Synthesis Example 1, except that 3-(4-bromophenyl)-9-phenyl-9H-carbazole (20.0 g, 50.21 mmol) and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (18.52 g, 51.22 mmol) were used as starting materials. (MS [M+H] + = 679)

[0184] Synthesis Example 3. Synthesis of Compound 1-3

[0185]

[0186] Compound 1-3 (27.8 g, 83.36% yield) was obtained in the same manner as in Synthesis Example 1, except that 3-(4'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-carbazole (20.0 g, 42.16 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1',4',1"-terphenyl]-4-amine (17.09 g, 43.00 mmol) were used as starting materials. (MS [M+H] + = 791)

[0187] Synthesis Example 4. Synthesis of Compound 1-4

[0188]

[0189] Compound 1-4 (26.2 g, 82.31% yield) was obtained in the same manner as in Synthesis Example 1, except that 3-(4'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-carbazole (20.0 g, 42.16 mmol) and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (15.54 g, 43.00 mmol) were used as starting materials. (MS [M+H] + = 755)

[0190] Synthesis Example 5. Synthesis of Compound 1-5

[0191]

[0192] Compound 1-5 (28.4 g, 83.22% yield) was obtained in the same manner as in Synthesis Example 1, except that 3-(4-bromophenyl)-9-(naphthalen-2-yl)-9H-carbazole (20.0 g, 44.61 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1',4',1"-terphenyl]-4-amine (18.09 g, 45.50 mmol) were used as starting materials. (MS [M+H] + = 765)

[0193] Synthesis Example 6. Synthesis of Compound 2-1

[0194]

[0195] After toluene (200ml) was added to 9-bromophenanthrene (15.0g, 58.34mmol), N-(4-(phenanthrene-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (25.08g, 59.50mmol) and sodium tert-butoxide (7.85g, 81.68mmol), the resultant was stirred for 10 minutes while heating. To the mixture was added bis(tri-tert-butylphosphine)palladium (BTP, 0.09g, 0.18mmol) dissolved in toluene (10ml), and the resultant was stirred for 1 hour while heating. After the reaction was terminated and the resultant was filtered, the layers were separated using toluene and water. After removing the solvent, the resultant was recrystallized with ethyl acetate to obtain compound 2-1 (25.5g, 73.12% yield). (MS[M+H]+=598)

[0196] Synthesis Example 7. Synthesis of Compound 2-2

[0197] Step 1) Synthesis of compound 2-2-A

[0198]

[0199] Dissolve bis(4-bromophenyl)amine (50.0 g, 152.90 mmol) and phenanthren-9-ylboronic acid (72.30 g, 321.08 mmol) in 1,4-dibromophenylamine. After the mixture was added to 1,4-dioxane (600 ml), a solution of potassium carbonate (105.66 g, 764.50 mmol: 300 ml of water) was added thereto, and the resultant was stirred for 10 minutes while heating. alkane (10ml) bis (tri-tert-butylphosphine) palladium (BTP, 0.23g, 0.46mmol), and the resultant was stirred for 1 hour while heating. After the reaction was terminated and the resultant was filtered, the layers were separated using chloroform and water. After removing the solvent, the resultant was recrystallized from ethyl acetate to obtain compound 2-2-A (65.0g, 81.49% yield).

[0200] Step 2) Synthesis of compound 2-2

[0201]

[0202] After toluene (250ml) was added to bromobenzene (10.00g, 63.69mmol), compound 2-2-A (33.89g, 64.96mmol) obtained in step 1 of synthesis example 7 and sodium tert-butoxide (8.57g, 89.17mmol), the resultant was stirred for 10 minutes while heating. Bis(tri-tert-butylphosphine)palladium (BTP, 0.11g, 0.21mmol) dissolved in toluene (10ml) was added to the mixture, and the resultant was stirred for 1 hour while heating. After the reaction was terminated and the resultant was filtered, the layers were separated using toluene and water. After removing the solvent, the resultant was recrystallized with ethyl acetate to obtain compound 2-2 (30.5g, 80.11% yield). (MS[M+H]+=598)

[0203] Synthesis Example 8. Synthesis of Compound 2-3

[0204] Compound 2-3 (35.8 g, 82.56% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 4-bromo-1,1'-biphenyl (15.0 g, 64.35 mmol) and Compound 2-2-A (34.24 g, 65.63 mmol) obtained in Step 1 of Synthesis Example 7 were used as starting materials. (MS [M+H] + = 674)

[0205] Synthesis Example 9. Synthesis of Compound 2-4

[0206]

[0207] Compound 2-4 (33.5 g, 77.25% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 2-bromo-1,1'-biphenyl (15.0 g, 64.35 mmol) and Compound 2-2-A (34.24 g, 65.63 mmol) obtained in Step 1 of Synthesis Example 7 were used as starting materials. (MS [M+H] + = 674)

[0208] Synthesis Example 10. Synthesis of Compound 2-5

[0209]

[0210] Compound 2-5 (28.8 g, 79.16% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 4-bromo-1,1':2',1"-terphenyl (15.0 g, 48.51 mmol) and Compound 2-2-A (25.81 g, 49.48 mmol) obtained in Step 1 of Synthesis Example 7 were used as starting materials. (MS [M+H] + = 750)

[0211] Synthesis Example 11. Synthesis of Compound 2-6

[0212]

[0213] Compound 2-6 (29.30 g, 80.54% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 5'-bromo-1,1':3',1"-terphenyl (15.0 g, 48.51 mmol) and Compound 2-2-A (25.81 g, 49.48 mmol) obtained in Step 1 of Synthesis Example 7 were used as starting materials. (MS [M+H] + = 750)

[0214] Synthesis Example 12. Synthesis of Compound 2-7

[0215]

[0216] Compound 2-7 (30.30 g, 77.29% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 2-bromo-9,9-dimethyl-9H-fluorene (15.0 g, 54.91 mmol) and Compound 2-2-A (29.22 g, 56.01 mmol) obtained in Step 1 of Synthesis Example 7 were used as starting materials. (MS [M+H] + = 714)

[0217] Synthesis Example 13. Synthesis of Compound 2-8

[0218] Compound 2-8 (30.0 g, 80.65% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 1-bromobenzene-2,3,4,5,6-d5 (10.0 g, 61.71 mmol) and Compound 2-2-A (32.84 g, 62.95 mmol) obtained in Step 1 of Synthesis Example 7 were used as starting materials. (MS [M+H] + = 603)

[0219] Synthesis Example 14. Synthesis of Compound 2-9

[0220]

[0221] Compound 2-9 (23.0 g, 81.55% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-d9 (10.0 g, 41.30 mmol) and Compound 2-2-A (21.97 g, 42.12 mmol) obtained in Step 1 of Synthesis Example 7 were used as starting materials. (MS [M+H] + = 683)

[0222] Synthesis Example 15. Synthesis of Compound 2-10

[0223]

[0224] Compound 2-10 (28.0 g, 80.00% yield) was obtained in the same manner as in Synthesis Example 6, except that 9-(3-chlorophenyl)phenanthrene (15.0 g, 51.94 mmol) and N-(4-(phenanthrene-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (22.33 g, 52.98 mmol) were used as starting materials. (MS [M+H] + = 674)

[0225] Synthesis Example 16. Synthesis of Compound 2-11

[0226] Step 1) Synthesis of Compound 2-11-A

[0227] Compound 2-11-A (58.0 g, 72.72% yield) was obtained in the same manner as in Step 1 of Synthesis Example 7, except that bis(3-bromophenyl)amine (50.0 g, 152.90 mmol) and phenanthrene-9-ylboronic acid (72.30 g, 321.08 mmol) were used as starting materials.

[0228] Step 2) Synthesis of Compound 2-11

[0229]

[0230] Compound 2-11 (32.8 g, 75.64% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 4-bromo-1,1'-biphenyl (15.00 g, 64.35 mmol) and Compound 2-11-A (34.24 g, 65.63 mmol) obtained in Step 1 of Synthesis Example 16 were used as starting materials. (MS [M+H] + = 674)

[0231] Synthesis Example 17. Synthesis of Compound 2-12

[0232] Step 1) Synthesis of Compound 2-12-A

[0233]

[0234] Compound 2-12-A (50.0 g, 73.33% yield) was obtained in the same manner as in Step 1 of Synthesis Example 7, except that 2-bromo-4'-chloro-1,1'-biphenyl (50.0 g, 186.88 mmol) and phenanthrene-9-ylboronic acid (43.57 g, 196.23 mmol) were used as starting materials.

[0235] Step 2) Synthesis of Compound 2-12

[0236] Compound 2-12 (32.0 g, 79.47% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that aniline (5.00 g, 53.69 mmol) and Compound 2-12-A (40.16 g, 110.06 mmol) obtained in Step 1 of Synthesis Example 17 were used as starting materials. (MS [M + H] + = 750)

[0237] Synthesis Example 18. Synthesis of Compound 2-13

[0238] Step 1) Synthesis of Compound 2-13-A

[0239]

[0240] Compound 2-13-A (30.0 g, 70.47% yield) was obtained in the same manner as in Step 1 of Synthesis Example 7, except that 9-bromophenanthrene (30.0 g, 116.67 mmol) and (4'-chloro-[1,1'-biphenyl]-4-yl)boric acid (28.48 g, 122.51 mmol) were used as starting materials.

[0241] Step 2) Synthesis of Compound 2-13

[0242]

[0243] Compound 2-13 (22.2 g, 80.14% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 9-(4'-chloro-[1,1'-biphenyl]-4-yl)phenanthrene (15.00 g, 41.11 mmol) and Compound 2-13-A (14.49 g, 41.93 mmol) obtained in Step 1 of Synthesis Example 18 were used as starting materials. (MS [M+H] + = 674)

[0244] Synthesis Example 19. Synthesis of Compound 2-14

[0245] Compound 2-14 (29.5 g, 81.09% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 4'-bromo-1,1':2',1"-terphenyl (15.0 g, 48.51 mmol) and Compound 2-2-A (25.81 g, 49.48 mmol) obtained in Step 1 of Synthesis Example 7 were used as starting materials. (MS [M+H] + = 750)

[0246] Synthesis Example 20. Synthesis of Compound 2-15

[0247]

[0248] Compound 2-15 (28.5 g, 78.33% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 2'-bromo-1,1':4',1"-terphenyl (15.0 g, 48.51 mmol) and Compound 2-2-A (25.81 g, 49.48 mmol) obtained in Step 1 of Synthesis Example 7 were used as starting materials. (MS [M+H] + = 750)

[0249] Synthesis Example 21. Synthesis of Compound 2-16

[0250] Compound 2-16 (29.3 g, 80.54% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 4'-bromo-1,1':3',1"-terphenyl (15.0 g, 48.51 mmol) and Compound 2-2-A (25.81 g, 49.48 mmol) obtained in Step 1 of Synthesis Example 7 were used as starting materials. (MS [M+H] + = 750)

[0251] Synthesis Example 22. Synthesis of Compound 2-17

[0252]

[0253] Compound 2-17 (30.0 g, 78.23% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 1-bromo-4-phenylnaphthalene (15.0 g, 52.97 mmol) and Compound 2-2-A (28.19 g, 54.03 mmol) obtained in Step 1 of Synthesis Example 7 were used as starting materials. (MS [M + H] + = 724)

[0254] Synthesis Example 23. Synthesis of Compound 2-18

[0255]

[0256] Compound 2-18 (22.0 g, 80.04% yield) was obtained in the same manner as in Step 2 of Synthesis Example 7, except that 9-(6-bromo-[1,1'-biphenyl]-3-yl)phenanthrene (15.0 g, 36.65 mmol) and N-(4-(phenanthrene-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (15.76 g, 37.38 mmol) were used as starting materials. (MS [M+H] + = 750)

[0257] 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.

[0258] <Examples and Comparative Examples>

[0259] Example 1

[0260] It is coated with a thickness of Indium tin oxide (ITO) of the present invention is placed in the distilled water dissolved with detergent and carries out ultrasonic cleaning as the glass substrate of film.In this article, 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 for 10 minutes twice.After finishing with distilled water cleaning, substrate is carried out ultrasonic cleaning with isopropyl alcohol, acetone and methanol solvent, 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.

[0261] On the transparent ITO electrode prepared as above, a compound represented by the following chemical formula HAT was thermally vacuum deposited onto The hole injection layer was formed by vacuum depositing the compound 1-1 prepared in Synthesis Example 1 onto the hole injection layer. The thickness of the hole transport layer is as follows, and the compound 2-1 prepared in Synthesis Example 6 is thermally vacuum deposited onto Subsequently, a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were vacuum deposited onto the substrate at a weight ratio of 25:1. Then, a compound represented by the following chemical formula HB1 is vacuum deposited onto Subsequently, a compound represented by the following chemical formula ET1 and a compound represented by the following LiQ were thermally vacuum deposited onto the substrate at a weight ratio of 1:1. The thickness of the film is used as a layer for both electron transport and electron injection. On the electron transport and electron injection layer, lithium fluoride (LiF) is sequentially deposited to The thickness and aluminum to A cathode is formed with a thickness of , thereby manufacturing an organic light emitting device.

[0262]

[0263] Examples 2 to 51 and Comparative Examples 1 to 9

[0264] The organic light-emitting devices of Examples 2 to 51 and Comparative Examples 1 to 9 were manufactured in the same manner as in Example 1, except that in Example 1, the compounds described in Table 1 below were used instead of Compound 1-1 as the hole transport layer, and the compounds described in Table 1 below were used instead of Compound 2-1 as the electron blocking layer. When 10 mA / cm 2 When the current was 100 0.05 ...

[0265] In the following Table 1, compounds HT1 and HT2 used as a hole transport layer are represented by the following chemical formulas HT1 and HT2, respectively, and compounds EB1 and EB2 used as an electron blocking layer are represented by the following chemical formulas EB1 and EB2, respectively.

[0266]

[0267] [Table 1]

[0268]

[0269]

[0270]

[0271]

[0272] As shown in Table 1, it was determined that the organic light emitting element using the compound represented by Chemical Formula 1 of the present disclosure as a hole transport layer and the compound represented by Chemical Formula 2 as an electron blocking layer was remarkably effective in terms of driving voltage, efficiency, and lifespan.

[0273] In particular, when Examples 1 to 16 and Comparative Example 1 are compared, the device including the hole transport layer using Compound 1-1 without the electron blocking layer using the compound of Chemical Formula 2 has high voltage and low efficiency, and in particular, has a significantly reduced lifespan.

[0274] When Examples 2, 18 and 34 utilizing both a hole transport layer and an electron blocking layer using the compound of the present disclosure were compared with Comparative Example 2 using only an electron blocking layer, it was determined that Examples 2, 18 and 34 had significantly longer lifespans and improved effects in voltage and efficiency.

[0275] Furthermore, when Comparative Examples 3 and 4 using HT1 in which two amine groups each replace the benzene ring of carbazole are compared with Examples 2 and 3, it is seen that Examples 2 and 3 in which only one amine group replaces the benzene ring of carbazole have characteristics of low voltage, high efficiency and long life.

[0276] Comparative Examples 5 and 6 use HT2 in which the benzene ring of carbazole not substituted with an amine group is substituted with deuterium. It is seen that Examples 3 and 5 using the compounds of the present disclosure in which the corresponding benzene ring is not substituted with deuterium exhibit characteristics of low voltage, high efficiency and long life.

[0277] Furthermore, it is seen that the organic light-emitting device of the present disclosure exhibits characteristics of low voltage, high efficiency, and long lifespan compared to Comparative Examples 7 to 9 using EB1 and EB2 in which the amine group is not substituted or substituted with one phenanthryl group.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one, two or more organic material layers disposed between the first electrode and the second electrode, The organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer comprising a compound of the following Chemical Formula 1 and an electron blocking layer comprising a compound of the following Chemical Formula 2: [Chemical formula 1] [Chemical formula 2] In Chemical Formulas 1 and 2, Ar1 to Ar4 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted with deuterium or an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms or an unsubstituted aryl group having 6 to 30 carbon atoms; R1 is hydrogen; R2 is hydrogen or deuterium; R3 to R8 are the same as or different from each other, and are each independently hydrogen, deuterium, or an unsubstituted aryl group having 6 to 30 carbon atoms; L1 to L7 are the same as or different from each other, and are each independently a direct bond, or a deuterium-substituted or unsubstituted arylene group having 6 to 30 carbon atoms; p1, q1, r1, s1, p2, q2 and r2 are each an integer from 0 to 2; When p1, q1, r1, s1, p2, q2 and r2 are 2, the substituents in the brackets are the same or different from each other; a is 4; e to h are integers from 0 to 4; b is an integer from 0 to 3; c and d are integers from 0 to 2; d+f≤5; c+g≤5; and When c and d are 2, the substituents in the brackets are the same or different from each other, When b, e, f are 2 or more, the substituents in the brackets are the same as or different from each other.

Images