Organic light-emitting devices

Abstract

The present specification relates to an organic light-emitting device, which includes: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer contains a compound of Chemical Formula 1 and a compound of Chemical Formula 2.

Description

Technical Field

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0164734 filed in the Korean Intellectual Property Office on December 11, 2019, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to an organic light emitting device including: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode. Background Art

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

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

[0005] Technical issues

[0006] The present specification is directed to providing an organic light emitting device including: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode.

[0007] Technical Solution

[0008] The present specification provides an organic light-emitting device, the organic light-emitting device comprising: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode.

[0009] The organic material layer includes a light-emitting layer, and the light-emitting layer includes a compound of the following Chemical Formula 1 and a compound of the following Chemical Formula 2.

[0010] [Chemical formula 1]

[0011]

[0012] [Chemical formula 2]

[0013]

[0014] In Chemical Formulas 1 and 2,

[0015] Ar1 to Ar4 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0016] A1 to A4 and R1 to R8 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted carbazolyl group, or bond with an adjacent group to form a substituted or unsubstituted ring,

[0017] Het is a substituted or unsubstituted heterocyclic group containing N, O or S having 5 to 20 carbon atoms,

[0018] L is a trivalent aromatic group having 5 to 20 carbon atoms,

[0019] a1 and a4 are each an integer from 1 to 4, and a2 and a3 are each an integer from 1 to 3,

[0020] When a1 to a4 are each an integer of 2 or more, two or more substituents in brackets are the same as or different from each other,

[0021] n is an integer of 0 or 1, and

[0022] When n is 0, N of carbazole is directly bonded to triazine.

[0023] Beneficial Effects

[0024] When the light emitting layer including the compounds of Chemical Formulas 1 and 2 according to an exemplary embodiment of the present specification is included, the service life of the organic light emitting device is improved.

[0025] When including a light emitting layer including the compounds of Chemical Formulas 1 and 2 according to an exemplary embodiment of the present specification, an organic light emitting device has an advantage of low driving voltage. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Figure 1 An organic light emitting device 10 according to an exemplary embodiment of the present specification is shown.

[0027] Figure 2 An organic light emitting device 11 according to another exemplary embodiment of the present specification is shown.

[0028] <Description of Reference Numerals>

[0029] 10, 11: Organic light-emitting devices

[0030] 20: Base

[0031] 30: First electrode

[0032] 40: Luminous layer

[0033] 50: Second electrode

[0034] 60: Hole injection layer

[0035] 70: Hole transport layer

[0036] 80: Electron transport layer

[0037] 90: Electron injection layer DETAILED DESCRIPTION

[0038] In the present specification, unless specifically described otherwise, when a part “includes” a constituent element, this does not mean excluding another constituent element but means that another constituent element may further be included.

[0039] In this specification, when one member is disposed “on” another member, this includes not only a case where one member is in contact with the other member but also a case where another member is present between the two members.

[0040] Examples of the substituent in the present specification will be described below, but are not limited thereto.

[0041] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of the substitution is not limited as long as the position is a position where the hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substitutions are made, the two or more substituents may be the same or different from each other.

[0042] In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the following: deuterium; halogen group; nitrile group; nitro group; hydroxyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylthio group; substituted or unsubstituted arylthio group; substituted or unsubstituted alkylsulfonyl group; substituted or unsubstituted arylsulfonyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted or unsubstituted amine group; substituted or unsubstituted arylphosphino group; substituted or unsubstituted phosphine oxide group; substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic group, or substituted with substituents connected by two or more substituents among the substituents exemplified above, or having no substituents. For example, "a substituent connected by two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent in which two phenyl groups are connected.

[0043] In this manual, It means a portion or a bonding portion that bonds to another substituent.

[0044] In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

[0045] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0046] In the present specification, the cycloalkyl group is not particularly limited but preferably has 3 to 30 carbon atoms, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0047] In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto.

[0048] In the present specification, the amine group can be selected from -NH2; alkylamine group; N-alkylarylamine group; arylamine group; N-arylheteroarylamine group; N-alkylheteroarylamine group; and heteroarylamine group, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl-anthrylamine, diphenylamine, N-phenylnaphthylamine, xylylamine, N-phenyltolylamine, triphenylamine, N-phenylbiphenylamine, N-phenylnaphthylamine, N-biphenylnaphthylamine, N-naphthylfluorenylamine, N-phenylphenanthrenylamine, N-biphenylphenanthrenylamine, N-phenylfluorenylamine, N-phenylterphenylamine, N-phenanthrenylfluorenylamine, N-biphenylfluorenylamine and the like, but are not limited thereto.

[0049] In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.

[0050] In the present specification, the N-arylheteroarylamine group means an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group.

[0051] In the present specification, the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group.

[0052] In the present specification, the alkyl group in the arylalkyl group, the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfonyl group and the N-alkylheteroarylamine group is the same as the above-mentioned example of the alkyl group. Specifically, examples of the alkylthio group include methylthio group, ethylthio group, tert-butylthio group, hexylthio group, octylthio group and the like, and examples of the alkylsulfonyl group include methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group and the like, but the examples are not limited thereto.

[0053] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 30. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl and the like, but are not limited thereto.

[0054] In the present specification, the arylalkenyl group means an alkenyl group substituted with an aryl group.

[0055] In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but are not limited thereto.

[0056] In this specification, the boron group can be -BR 100 R 101 , R 100 and R 101 are the same as or different from each other and may each be independently selected from hydrogen; deuterium; halogen; nitrile; substituted or unsubstituted monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms; substituted or unsubstituted straight-chain or branched alkyl having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl having 2 to 30 carbon atoms.

[0057] In the present specification, specific examples of the phosphine oxide group include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, 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 thereof is not particularly limited, but is preferably 6 to 30. Specific examples of the monocyclic aryl group include phenyl, biphenyl, terphenyl and the like, but are not limited thereto.

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

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

[0062] When the fluorenyl group is substituted, the substituent may be etc. However, the substituent is not limited thereto.

[0063] In this specification, an "adjacent" group may mean a substituent that replaces an atom directly connected to an atom substituted by a corresponding substituent, a substituent that is disposed closest to a corresponding substituent in space, or another substituent that replaces an atom substituted by a corresponding substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents that replace the same carbon in an aliphatic ring may be interpreted as groups "adjacent" to each other.

[0064] In the present specification, the aryl in arylalkyl, arylalkenyl, aryloxy, arylthio, arylsulfonyl, N-arylalkylamine, N-arylheteroarylamine and arylphosphino is the same as the above-mentioned example of aryl. Specifically, examples of aryloxy include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethylphenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 1-phenanthrenyloxy, 3-phenanthrenyloxy, 9-phenanthrenyloxy, etc., examples of arylthio include phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc., examples of arylsulfonyl include benzenesulfonyl, p-toluenesulfonyl, etc., but examples are not limited thereto.

[0065] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, or substituted or unsubstituted triarylamine groups. The aryl group in the arylamine group can be a monocyclic aryl group or a polycyclic aryl group. The arylamine group comprising two or more aryl groups can comprise a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group can be selected from the above-mentioned examples of aryl groups.

[0066] In the present specification, the heteroaryl group contains one or more atoms other than carbon, i.e., one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heterocyclic groups 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 (phenanthroline), thiazolyl, isothiophene Azolyl, oxadiazole, thiadiazolyl, benzothiazolyl, phenothiazinyl, phen oxazine, dibenzofuranyl, etc., but are not limited thereto.

[0067] In this specification, examples of heteroarylamine groups include substituted or unsubstituted monoheteroarylamine groups, substituted or unsubstituted diheteroarylamine groups, or substituted or unsubstituted triheteroarylamine groups. Heteroarylamine groups containing two or more heteroaryl groups may contain monocyclic heteroaryl groups, polycyclic heteroaryl groups, or both monocyclic heteroaryl groups and polycyclic heteroaryl groups. For example, the heteroaryl groups in the heteroarylamine groups may be selected from the above examples of heteroaryl groups.

[0068] In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the above-mentioned examples of the heteroaryl group.

[0069] In the present specification, the arylene group means a group having two bonding positions in an aryl group, that is, a divalent group. The above description about the aryl group can be applied to the arylene group, except that the arylene groups are each a divalent group.

[0070] According to an exemplary embodiment of the present specification, there is provided an organic light emitting device including: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound of Chemical Formula 1 and a compound of Chemical Formula 2. In this case, the first electrode and the second electrode may be disposed to face each other.

[0071] According to an exemplary embodiment of the present specification, the compound of Chemical Formula 1 is the following Chemical Formula 1-1.

[0072] [Chemical formula 1-1]

[0073]

[0074] In Chemical Formula 1-1, Ar1, Ar2, A1 to A4, and a1 to a4 are the same as defined in Chemical Formula 1.

[0075] According to an exemplary embodiment of the present specification, the compound of Chemical Formula 1 is any one of the following Chemical Formulas 1-1-1 to 1-1-3.

[0076] [Chemical formula 1-1-1]

[0077]

[0078] [Chemical formula 1-1-2]

[0079]

[0080] [Chemical formula 1-1-3]

[0081]

[0082] In Chemical Formulas 1-1-1 to 1-1-3,

[0083] Ar1, Ar2 and Ar5 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,

[0084] A5 to A11 and A14 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group,

[0085] A12 and A13 are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,

[0086] a5, a6, a8 and a9 are each an integer from 1 to 3, and a7, a10 and a11 are each an integer from 1 to 4,

[0087] When a5 to a11 are each an integer of 2 or more, two or more structures in the brackets are the same as or different from each other, and

[0088] a14 is 1 or 2, and when a14 is 2, the structures in the brackets are the same as or different from each other.

[0089] According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted phenanthryl group.

[0090] According to an exemplary embodiment of 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; a terphenyl group; a naphthyl group; or a phenanthryl group.

[0091] According to an exemplary embodiment of the present specification, A1 to A4 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted carbazole group, or bond with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring.

[0092] According to an exemplary embodiment of the present specification, A1 to A4 are the same as or different from each other, and are each independently hydrogen; or deuterium.

[0093] According to an exemplary embodiment of the present specification, A1 to A4 are the same as or different from each other, and are each independently hydrogen.

[0094] According to an exemplary embodiment of the present specification, A5 to A11 and A14 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0095] According to an exemplary embodiment of the present specification, A5 to A11 and A14 are the same as or different from each other, and are each independently hydrogen; or deuterium.

[0096] According to an exemplary embodiment of the present specification, A5 to A11 and A14 are the same as or different from each other, and are each independently hydrogen.

[0097] According to an exemplary embodiment of the present specification, A12 and A13 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0098] According to an exemplary embodiment of the present specification, A12 and A13 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group.

[0099] According to an exemplary embodiment of the present specification, A12 and A13 are the same as or different from each other, and are each independently an alkyl group.

[0100] According to an exemplary embodiment of the present specification, A12 and A13 are methyl groups.

[0101] According to an exemplary embodiment of the present specification, Ar5 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted phenanthryl group.

[0102] According to an exemplary embodiment of the present specification, Ar5 is a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; or a phenanthryl group.

[0103] According to an exemplary embodiment of the present specification, Ar5 is a phenyl group.

[0104] According to an exemplary embodiment of the present specification, Chemical Formula 1 is selected from the following compounds.

[0105]

[0106]

[0107] According to an exemplary embodiment of the present specification, the compound of Chemical Formula 2 is the following Chemical Formula 2-1.

[0108] [Chemical formula 2-1]

[0109]

[0110] In Chemical Formula 2-1, Ar3, Ar4 and Het are the same as those defined in Chemical Formula 2,

[0111] R1 to R9 are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group, and

[0112] r9 is an integer of 1 to 3, and when r9 is an integer of 2 or more, two or more structures in the brackets are the same as or different from each other.

[0113] According to an exemplary embodiment of the present specification, the compound of Chemical Formula 2 is the following Chemical Formula 2-2.

[0114] [Chemical formula 2-2]

[0115]

[0116] In chemical formula 2-2,

[0117] Ar3, Ar4, Ar6 and Ar7 are the same as or different from each other and are each independently substituted or unsubstituted aryl,

[0118] At least one of X1 to X3 is N, and the rest are CH,

[0119] R1 to R9 are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group, and

[0120] r9 is an integer of 1 to 3, and when r9 is an integer of 2 or more, two or more structures in the brackets are the same as or different from each other.

[0121] According to an exemplary embodiment of the present specification, the compound of Chemical Formula 2 is any one of the following Chemical Formulas 2-2-1 to 2-2-3.

[0122] [Chemical formula 2-2-1]

[0123]

[0124] [Chemical formula 2-2-2]

[0125]

[0126] [Chemical formula 2-2-3]

[0127]

[0128] In chemical formulas 2-2-1 to 2-2-3,

[0129] Ar3, Ar4, Ar6 and Ar7 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group,

[0130] At least one of X1 to X3 is N, and the rest are CH,

[0131] R1 to R9 are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group, and

[0132] r9 is an integer of 1 to 3, and when r9 is an integer of 2 or more, two or more structures in the brackets are the same as or different from each other.

[0133] According to an exemplary embodiment of the present specification, at least two of X1 to X3 are N, and the rest are CH.

[0134] According to an exemplary embodiment of the present specification, X1 to X3 are N.

[0135] According to an exemplary embodiment of the present specification, Ar3, Ar4, Ar6, and Ar7 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.

[0136] According to an exemplary embodiment of the present specification, Ar3, Ar4, Ar6, and Ar7 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms.

[0137] According to an exemplary embodiment of the present specification, Ar3, Ar4, Ar6, and Ar7 are phenyl groups.

[0138] According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; deuterium; or an aryl group.

[0139] According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; deuterium; or a phenyl group.

[0140] According to an exemplary embodiment of the present specification, R9 is hydrogen; or deuterium.

[0141] According to an exemplary embodiment of the present specification, R9 is hydrogen.

[0142] According to an exemplary embodiment of the present specification, Chemical Formula 2 is selected from the following compounds.

[0143]

[0144] According to an exemplary embodiment of the present specification, the organic material layer of the organic light-emitting device of the present specification may be composed of a single-layer structure, but may also be composed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light-emitting device is not limited thereto, and may include fewer or more organic layers.

[0145] The organic light emitting device may have a stack structure, for example, as described below, but the stack structure is not limited thereto.

[0146] (1) Positive electrode / hole transport layer / light-emitting layer / negative electrode

[0147] (2) Positive electrode / hole injection layer / hole transport layer / light-emitting layer / negative electrode

[0148] (3) Positive electrode / hole transport layer / light-emitting layer / electron transport layer / negative electrode

[0149] (4) Positive electrode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / negative electrode

[0150] (5) Positive electrode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / negative electrode

[0151] (6) Positive electrode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / negative electrode

[0152] (7) Positive electrode / hole transport layer / electron blocking layer / luminescent layer / electron transport layer / negative electrode

[0153] (8) Positive electrode / hole transport layer / electron blocking layer / luminescent layer / electron transport layer / electron injection layer / negative electrode

[0154] (9) Positive electrode / hole injection layer / hole transport layer / electron blocking layer / luminescent layer / electron transport layer / negative electrode

[0155] (10) Positive electrode / hole injection layer / hole transport layer / electron blocking layer / luminescent layer / electron transport layer / electron injection layer / negative electrode

[0156] (11) Positive electrode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / negative electrode

[0157] (12) Positive electrode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / negative electrode

[0158] (13) Positive electrode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / negative electrode

[0159] (14) Positive electrode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / negative electrode

[0160] (15) Positive electrode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / negative electrode

[0161] (16) Positive electrode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport and injection layer / negative electrode

[0162] (17) Positive electrode / hole injection layer / first hole transport layer / second hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport and injection layer / negative electrode

[0163] (18) Positive electrode / hole injection layer / first hole transport layer / second hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / negative electrode

[0164] (19) Positive electrode / hole injection layer / first hole transport layer / second hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / negative electrode / covering layer

[0165] For example, the structure of the organic light-emitting device of the present specification can be Figure 1 and Figure 2 The structure shown in, but not limited to.

[0166] Figure 1 The structure of the organic light emitting device 10 in which the first electrode 30 , the light emitting layer 40 , and the second electrode 50 are sequentially stacked on the substrate 20 is illustrated. Figure 1 is an exemplary structure of an organic light emitting device according to an exemplary embodiment of the present specification, and may further include an additional organic material layer.

[0167] Figure 2The structure of the organic light emitting device 11 in which the first electrode 30 , the hole injection layer 60 , the hole transport layer 70 , the light emitting layer 40 , the electron transport layer 80 , the electron injection layer 90 , and the second electrode 50 are sequentially stacked on the substrate 20 is illustrated. Figure 2 is an exemplary structure according to an exemplary embodiment of the present specification, and the structure may further include an additional organic material layer.

[0168] According to an exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant, and the host includes a compound of Chemical Formula 1 and a compound of Chemical Formula 2.

[0169] In the light emitting layer, the weight ratio of the compound of Chemical Formula 1 to the compound of Chemical Formula 2 is preferably 99:1 to 1:99, or 95:5 to 5:95.

[0170] In an exemplary embodiment of the present specification, the light emitting layer includes the compounds of Chemical Formulas 1 and 2 as a host, and may include another organic compound, metal, or metal compound as a dopant.

[0171] According to an exemplary embodiment of the present specification, the organic material layer may further include one or more layers selected from a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0172] The organic light-emitting device of the present specification can be manufactured by materials and methods known in the art, except that the light-emitting layer includes the heterocyclic compounds of Chemical Formulas 1 and 2.

[0173] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0174] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation to form a first electrode, 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 first electrode, and then depositing a material that can be used as a second electrode on the organic material layer. In addition to the above method, the organic light-emitting device can also be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.

[0175] In addition, when manufacturing an organic light-emitting device, the compounds of Chemical Formulas 1 and 2 can be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0176] According to an exemplary embodiment of the present specification, the first electrode is a positive electrode, and the second electrode is a negative electrode.

[0177] According to another exemplary embodiment of the present specification, the first electrode is a negative electrode, and the second electrode is a positive electrode.

[0178] As the positive electrode material, a material with a high work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; etc., but are not limited thereto.

[0179] As the negative electrode material, a material having a low work function is generally preferred to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al and Mg / Ag; etc., but are not limited thereto.

[0180] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, and therefore has the effect of injecting holes at the positive electrode and the effect of excellently injecting holes into the luminescent layer or luminescent material, preventing the excitons generated by the luminescent layer from moving to the electron injection layer or the electron injection material, and the ability to form a thin film is also excellent. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the positive electrode material and the HOMO of the 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, conductive polymers based on polyaniline and polythiophene, etc., but are not limited thereto.

[0181] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is suitably a material having high hole mobility that can receive holes from the positive electrode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0182] The electron blocking layer is a layer that can improve the service life and efficiency of the device by preventing the electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer, and can be formed at an appropriate portion between the light-emitting layer and the hole injection layer by using a known electron-rich material, if necessary. The material for the electron blocking layer needs to be selected in consideration of the characteristics of the light-emitting layer adjacent to the entire device structure, and is generally selected from materials that can generally be used as materials for the hole transport layer.

[0183] According to an exemplary embodiment of the present specification, the compound of the following EBL1 is preferably selected for the electron blocking layer adjacent to the light-emitting layer containing the compound of Chemical Formula 1 and the compound of Chemical Formula 2. The electron transport layer material in which the electrons are sufficiently charged to match the material used for the light-emitting layer is used to make the light-emitting layer electron-rich, so that the effect of the present invention of improving the light-emitting efficiency is shown, but there is a problem that the electrons rich in the light-emitting layer enter the hole transport layer and thus deteriorate the hole transport layer. Therefore, in the device structure of the present specification, the electron blocking layer is indispensable, and the following EBL1 as a hole-rich material is used to prevent the outflow of electrons from the light-emitting layer, so that a long service life and high efficiency can be achieved by preventing the hole transport layer from deteriorating.

[0184]

[0185] The light-emitting material used for the light-emitting layer 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 them, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. In the present specification, the compounds of Chemical Formulas 1 and 2 are included, and another additional light-emitting material may also be included. 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.

[0186] The light-emitting layer may include a host material and a dopant material. The host material includes compounds of Chemical Formulas 1 and 2, and may further include another additional light-emitting material. Examples of additional light-emitting materials include fused aromatic ring derivatives or heterocyclic compounds, etc. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but examples thereof are not limited thereto.

[0187] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and examples thereof include pyrene, anthracene, The styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino groups are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, examples of metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0188] According to an exemplary embodiment of the present specification, the light emitting layer further includes a phosphorescent dopant.

[0189] According to an exemplary embodiment of the present specification, the phosphorescent dopant may be a metal complex.

[0190] According to an exemplary embodiment of the present specification, examples of the phosphorescent dopant include iridium complexes, platinum complexes, and the like, but are not limited thereto.

[0191] According to an exemplary embodiment of the present specification, the phosphorescent dopant may be any one of the following compounds, but is not limited thereto.

[0192]

[0193]

[0194] The hole blocking layer is a layer that can improve the service life and efficiency of the device by preventing holes injected from the hole injection layer from passing through the light-emitting layer and entering the electron injection layer, and if necessary, can be formed at an appropriate portion between the light-emitting layer and the electron injection layer by using a known material.

[0195] 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 the electron transport material is suitably a material with high electron mobility that can skillfully receive electrons from the negative electrode and transport the electrons to the light-emitting layer. Specific examples thereof include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the relevant technology. In particular, examples of suitable cathode materials include typical materials with low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0196] The electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound that has the ability to transport electrons, the effect of injecting electrons from the negative electrode, and the excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated by the light-emitting layer from moving to the hole injection layer, and is also excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone and the like and their derivatives, metal complex compounds, nitrogen-containing five-membered ring derivatives and the like, but not limited thereto.

[0197] Examples of metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, 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.

[0198] The cover layer is deposited protrudingly on the transparent cathode, and thus serves to collect light emitted from the cathode. The electrical properties of the organic material forming the cover layer are not an item to be considered, but the refractive index of the formed film is important. Under the wavelength condition of 520nm, the refractive index required for the cover layer may be 1.96 or less and 1.93 or more, and preferably 1.94.

[0199] The organic material forming the cover layer is not particularly limited but may be selected from the following compounds, for example.

[0200]

[0201] 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.

[0202] According to an exemplary embodiment of the present specification, the compounds of Chemical Formulas 1 and 2 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[0203] Embodiments of the invention

[0204] Hereinafter, the present specification will be described in detail with reference to the embodiments for specifically describing the present specification. However, the embodiments according to the present specification can be modified in various forms, and the scope of the present specification should not be interpreted as being limited to the embodiments described in detail below. The embodiments of the present specification are provided to more completely illustrate the present specification to those of ordinary skill in the art.

[0205] [Synthesis example 1]

[0206]

[0207] Compound 1-1-A (46.6mmol), compound 1-1-B (51.3mmol), potassium carbonate (139.8mmol) and tetrakis (triphenylphosphine) palladium (0) (0.9mmol) were placed in tetrahydrofuran, and the resulting mixture was refluxed for 12 hours. After the reaction was completed, the water layer was removed, the organic layer was dried over magnesium sulfate, and the filtrate was then distilled under reduced pressure. After the obtained solid was dissolved in chloroform (500ml), ethyl acetate (100ml) was added thereto, and the resulting mixture was recrystallized and then dried to obtain compound 1-1 (yield 86%).

[0208] [Synthesis example 2]

[0209]

[0210] Compound 1-2 was synthesized in the same manner as in Synthesis Example 1, except that in Synthesis Example 1, Compound 1-2-A and Compound 1-2-B (102.6 mmol) were used instead of Compound 1-1-A and Compound 1-1-B (51.3 mmol), respectively.

[0211] [Synthesis example 3]

[0212]

[0213] Compound 1-4 was synthesized in the same manner as in Synthesis Example 1, except that in Synthesis Example 1, Compound 1-4-A and Compound 1-4-B were used instead of Compound 1-1-A and Compound 1-1-B, respectively.

[0214] [Synthesis Example 4]

[0215]

[0216] Compound 1-9 was synthesized in the same manner as in Synthesis Example 1, except that in Synthesis Example 1, Compound 1-9-A and Compound 1-9-B were used instead of Compound 1-1-A and Compound 1-1-B, respectively.

[0217] [Synthesis Example 5]

[0218]

[0219] Compound 1-11 was synthesized in the same manner as in Synthesis Example 1, except that in Synthesis Example 1, Compound 1-11-A and Compound 1-11-B were used instead of Compound 1-1-A and Compound 1-1-B, respectively.

[0220] [Synthesis example 6]

[0221]

[0222] K2CO3 (4.91mmol) and 2-4-B (3.93mmol) were placed in N-methylpyrrolidone (NMP), and the resulting mixture was stirred at room temperature for 1 hour. Compound 2-4-A (0.655mmol) was added thereto. The mixture was stirred at 180°C for 18 hours. The mixture was stirred again at 195°C for 11 hours. The reaction mixture was quenched with H2O, the precipitated product was filtered, and then washed with methanol (MeOH). The filtered product was purified again by silica gel column chromatography (hexane: toluene = 1: 1) to obtain compound 2-4 (0.422mmol) as a white powder with a yield of 64%.

[0223] [Synthesis Example 7]

[0224]

[0225] Compound 2-3 was synthesized in the same manner as in Synthesis Example 6, except that in Synthesis Example 6, Compound 2-3-A and Compound 2-3-B were used instead of Compound 2-4-A and Compound 2-4-B, respectively.

[0226] [Synthesis example 8]

[0227]

[0228] Compound 2-5 was synthesized in the same manner as in Synthesis Example 6, except that in Synthesis Example 6, Compound 2-5-A and Compound 2-5-B were used instead of Compound 2-4-A and Compound 2-4-B, respectively.

[0229] [Synthesis Example 9]

[0230]

[0231] Compound 2-6 was synthesized in the same manner as in Synthesis Example 6, except that in Synthesis Example 6, Compound 2-6-A and Compound 2-6-B were used instead of Compound 2-4-A and Compound 2-4-B, respectively.

[0232] [Synthesis Example 10]

[0233]

[0234] After dispersing 9-([1,1'-biphenyl]-3-yl)-3-bromo-9H-carbazole) (20.0 g, 50.4 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazole-3-yl)boric acid (18.3 g, 50.4 mmol) in tetrahydrofuran (250 ml), 2M potassium carbonate aqueous solution (K2CO3 aqueous solution) (50.4 ml, 100.7 mmol) was added thereto, tetrakistriphenylphosphine palladium [Pd(PPh3)4] (1.7 g, 3 mol%) was put therein, and then the resulting mixture was stirred and refluxed for 4 hours. The temperature was lowered to room temperature, and the generated solid was filtered. The filtered solid was recrystallized with chloroform and ethyl acetate, filtered, and then dried to prepare compound 1-12 (21.5 g, yield 67%, MS: [M+H] + =637).

[0235] [Comparative Example 1]

[0236] As an anode, a substrate on which Ag / ITO was deposited to a thickness of 100nm / 5nm was cut into a size of 100mm×100mm×0.5mm, placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. A product manufactured by Fischer Co. was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After washing with distilled water was completed, ultrasonic washing was performed in this order using isopropyl alcohol, acetone, and methanol solvents, and then dried.

[0237] On the anode thus prepared, HTL1 was thermally vacuum deposited to have and co-deposited with PD1 (2 wt %) to form a hole injection layer (HIL1). (Deposition rate: (HTL1), (PD1)

[0238]

[0239] On the hole injection layer, only HTL1 is vacuum deposited to have The thickness of the first hole transport layer (HTL1) is formed, and the following HT-A is vacuum deposited onto the surface having The thickness of the second hole transport layer (HTL2) is formed. (Deposition rate: )

[0240]

[0241] Then, the following EBL1 is vacuum deposited onto the The thickness of the electron blocking layer (EBL) is formed. (Deposition rate: )

[0242]

[0243] On the electron blocking layer, a compound P-host A (a P-type host) and a compound N-host A (an N-type host) as a host (the weight ratio of P-host A:N-host A=6:4) and the following iridium compound (GD) (6 wt%) as a dopant are vacuum deposited onto a substrate having a surface having a thickness of 100 nm. The thickness of the film is 200 nm, thereby forming an emitting layer (EML). (Deposition rate: (P-Principal A), (N-Entity A), (GD)

[0244]

[0245] Thereafter, HBL1 was vacuum deposited onto a The thickness of the film is 2000 nm, thereby forming a hole blocking layer (HBL), and ETL1 and Liq are vacuum deposited at a weight ratio of 2:1 to form an electron transport layer (ETL). (Deposition rate: (HBL1), (ETL1), (Liq)

[0246]

[0247] Subsequently, ytterbium (Yb) and lithium fluoride (LiF) are deposited on the After forming a film as an electron injection layer (EIL) with a thickness of , magnesium and silver (1:4) were used to form a film with a thickness of The cathode is then deposited with the following CPL The thickness of the coating is used as a cover layer to complete the device. (Deposition rate: (Yb, LiF), (Ag), (Mg)

[0248]

[0249] [Examples 1 to 9 and Comparative Examples 2 to 7]

[0250] Devices of Examples 1 to 9 and Comparative Examples 2 to 7 were each manufactured in the same manner as in Comparative Example 1, except that in Comparative Example 1, the compounds shown in Table 1 were each used as the P-type body and the N-type body.

[0251]

[0252] [Experimental example]

[0253] By 1.0E -7 The experiment was conducted by evaporating OLED organic compounds in a vacuum chamber of 10000 ℃ or higher. After the encapsulation process was completed, baking was carried out in an oven at 110°C for 40 minutes. In this case, the aging effect of the organic film can be seen by baking, so that a stable top-emitting organic EL device can be obtained.

[0254] The IVL characteristics of the fully baked organic EL device were measured using a PR-670IVL measuring instrument manufactured by Photo Research Inc., and the lifespan (LT) of the upper organic EL device was measured by a photodiode method based on 20,000 nits using the M6000 product manufactured by McScience, and the time required for the brightness to drop from the initial brightness to 95% was shown as T95.

[0255] [Table 1]

[0256]

[0257] *V: driving voltage

[0258] *cd / A: efficiency

[0259] According to the results in Table 1, it can be determined that Examples 1 to 4 satisfy low voltage, high efficiency or long service life compared with Comparative Examples 1 to 5.

[0260] It can be confirmed that in the case of Example 1, due to the combination of the subject matter described in this specification, even if the driving voltage is increased by 0.3 V, the service life of 100 hours of Comparative Examples 1 to 3 is significantly extended to 500 hours.

[0261] It can be confirmed that the efficiencies of Examples 1 to 4 are maintained at a level similar to that of the Comparative Example, but the driving voltage is reduced and the service life is greatly improved.

[0262] As shown in Comparative Example 5, it can be confirmed that a combination using an N-type host similar to Chemical Formula 2 of the present specification has a longer lifespan, but has a higher voltage and lower efficiency.

[0263] It can be determined that when Example 5 in which Compound 2-3 is used and Comparative Example 5 in which Compound 3-2 is used are compared, as an N-type host, Compound 3-2 increases the service life by connecting triazine having a large number of electrons with a material having a certain amount of holes (such as dibenzofuran or dibenzothiophene) to control the flow of electrons, but the electrons cannot flow smoothly, so the voltage increases.

[0264] Compounds 3-1 and 3-2 have large volumes due to their larger molecular weight than compound 2-3, and during mass production of panels, sublimation of the material causes problems in mass production. Specifically, the preferred material should melt or remain powdery when heated, but compounds 3-1 and 3-2 harden to the top of the crucible like hard cotton, so that the material does not sublime.

[0265] [Example 10, Example 11, Comparative Example 8 and Comparative Example 9]

[0266] Devices of Example 10, Example 11, Comparative Example 8 and Comparative Example 9 were each manufactured in the same manner as in Example 7, except that in Example 7, the compounds shown in Table 2 were each used as the P-type main body, N-type main body, electron blocking layer and capping layer.

[0267]

[0268] By 1.0E -7 The experiment was conducted by evaporating OLED organic compounds in a vacuum chamber of 10000 ℃ or higher. After the encapsulation process was completed, baking was carried out in an oven at 110°C for 40 minutes. In this case, the aging effect of the organic film can be seen by baking, so that a stable top-emitting organic EL device can be obtained.

[0269] The IVL characteristics of the fully baked organic EL device were measured using a PR-670IVL measuring instrument manufactured by Photo Research Inc., and the lifespan (LT) of the upper organic EL device was measured by a photodiode method based on 20,000 nits using the M6000 product manufactured by McScience, and the time required for the brightness to drop from the initial brightness to 95% was shown as T95.

[0270] [Table 2]

[0271]

[0272] It was determined that Examples 10 and 11 using Compounds 3-6 and 3-5, respectively, had shorter service lives than Example 7 using EBL1 as a hole blocking layer. It was determined that the service life was shortened to some extent due to the degradation of the hole transport layer using Compound 3-5 or Compound 3-6 having lower hole transport properties than EBL1.

[0273] Since the N-type host of the present application is composed of two triazines, the amount of electrons becomes relatively too dominant relative to holes, so that the energy balance of electrons and holes in the light-emitting layer is mismatched, but the hole-rich EBL1 is used in the EBL layer adjacent to the light-emitting layer to restore the lost balance in the light-emitting layer. Therefore, compared with Comparative Example 8 in which Compound 3-3 having one triazine is used, Example 7 in which EBL1 is used to produce a balance shows better performance.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode; as well as an organic material layer having one or more layers disposed between the first electrode and the second electrode, The organic material layer includes a light-emitting layer, and the light-emitting layer includes a compound of the following chemical formula 1 and a compound of the following chemical formula 2-2: [Chemical formula 1] [Chemical formula 2-2] In Chemical Formulas 1 and 2-2, Ar1 and Ar2 are the same as or different from each other and are each independently a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms, A1 to A4 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 substituted or unsubstituted with deuterium, or a carbazolyl group which is substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms or deuterium, or are bonded to an adjacent group to form a ring which is substituted or unsubstituted with one or two or more substituents selected from deuterium, an alkyl group having 1 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms, a1 and a4 are each an integer from 1 to 4, and a2 and a3 are each an integer from 1 to 3, When a1 to a4 are each an integer of 2 or more, two or more substituents in brackets are the same as or different from each other, Ar3, Ar4, Ar6 and Ar7 are the same as or different from each other and are each independently a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms, X1 to X3 are N, R1 to R9 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 may be substituted with or without deuterium, r9 is an integer of 1 to 3, and when r9 is an integer of 2 or more, two or more structures in the brackets are the same as or different from each other.

2. The organic light-emitting device according to claim 1, wherein the compound of Chemical Formula 1 is the following Chemical Formula 1-1: [Chemical formula 1-1] In Chemical Formula 1-1, Ar1, Ar2, A1 to A4, and a1 to a4 are the same as defined in Chemical Formula 1.

3. The organic light-emitting device according to claim 1, wherein the compound of Chemical Formula 1 is any one of the following Chemical Formulas 1-1-1 to 1-1-3: [Chemical formula 1-1-1] [Chemical formula 1-1-2] [Chemical formula 1-1-3] In Chemical Formulas 1-1-1 to 1-1-3, Ar1, Ar2 and Ar5 are the same as or different from each other and are each independently a deuterium-substituted or unsubstituted aryl group having 6 to 20 carbon atoms, A5 to A11 and A14 are the same as or different from each other, and are each independently hydrogen, deuterium, or a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms, A12 and A13 are the same as or different from each other and are each independently a deuterium-substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a5, a6, a8 and a9 are each an integer from 1 to 3, and a7, a10 and a11 are each an integer from 1 to 4, When a5 to a11 are each an integer of 2 or more, two or more structures in the brackets are the same as or different from each other, and a14 is 1 or 2, and when a14 is 2, the structures in the brackets are the same as or different from each other.

4. The organic light-emitting device according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and are each independently a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted terphenyl group, a deuterium-substituted or unsubstituted naphthyl group, or a deuterium-substituted or unsubstituted phenanthryl group.

5. The organic light-emitting device according to claim 1, wherein the compound of Chemical Formula 2-2 is any one of the following Chemical Formulas 2-2-1 to 2-2-3: [Chemical formula 2-2-1] [Chemical formula 2-2-2] [Chemical formula 2-2-3] In chemical formulas 2-2-1 to 2-2-3, Ar3, Ar4, Ar6 and Ar7 are the same as or different from each other and are each independently a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms, At least one of X1 to X3 is N, and the rest are CH, R1 to R9 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 may be substituted with or without deuterium, and r9 is an integer of 1 to 3, and when r9 is an integer of 2 or more, two or more structures in the brackets are the same as or different from each other.

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

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

8. The organic light emitting device according to claim 1, wherein the light emitting layer comprises a host and a dopant, The host includes a compound of Chemical Formula 1 and a compound of Chemical Formula 2-2, and The dopant is a phosphorescent dopant.

9. The organic light emitting device according to claim 8, wherein the phosphorescent dopant is any one of the following compounds:

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