Organic light emitting device

Abstract

The present specification relates to an organic light-emitting device comprising: an anode; a cathode; a light emitting layer disposed between the anode and the cathode; a first organic layer disposed between the anode and the light emitting layer and including a compound of chemical formula 1; and a second organic layer disposed between the anode and the light emitting layer and including a compound of chemical formula 2.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2023-0014714 filed with the Korean Patent Office on February 3, 2023, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to organic light emitting devices. Background Art

[0003] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting generally has a structure including an anode and a cathode and an organic layer located between them. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the invention

[0005] Technical issues

[0006] This specification provides an organic light-emitting device.

[0007] Solution to the problem

[0008] The present invention provides an organic light-emitting device, which includes: an anode; a cathode; a light-emitting layer arranged between the anode and the cathode; a first organic layer arranged between the anode and the light-emitting layer and containing a compound of the following chemical formula 1; and a second organic layer arranged between the anode and the light-emitting layer and containing a compound of the following chemical formula 2.

[0009] [Chemical formula 1]

[0010]

[0011] [Chemical formula 2]

[0012]

[0013] In the above chemical formulas 1 and 2,

[0014] Ar1 is a substituted or unsubstituted aryl group,

[0015] Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted heteroaryl group,

[0016] Ar4 is a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring formed by condensing these groups.

[0017] Ar5 is unsubstituted naphthyl or unsubstituted phenanthrenyl,

[0018] R1 to R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0019] R5 and R6 are the same or different from each other and are each independently hydrogen, deuterium or aryl,

[0020] L1 to L5 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0021] a and c to f are integers from 0 to 4,

[0022] b is an integer from 0 to 3,

[0023] When a to f are 2 or more, R1 to R6 are the same as or different from each other.

[0024] p, q, r, s and t are each an integer from 0 to 2,

[0025] When p to t are 2 or more, L1 to L5 are the same as or different from each other.

[0026] Effects of the Invention

[0027] The organic light emitting device according to one embodiment of the present specification shows a lower driving voltage by adjusting the potential barrier between organic layers by appropriately adjusting the HOMO and LUMO energies of the compound, and efficiency and lifespan may be improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 An organic light emitting device according to one embodiment of the present specification is illustrated.

[0029] Figure 2 An organic light emitting device according to one embodiment of the present specification is illustrated.

[0030] [Explanation of symbols]

[0031] 1: Substrate

[0032] 2: Anode

[0033] 3: First hole transport layer

[0034] 4: Second hole transport layer

[0035] 5: Luminous layer

[0036] 6: Cathode

[0037] 7: Hole injection layer

[0038] 8: Hole suppression layer

[0039] 9: Electron injection and transport layer DETAILED DESCRIPTION

[0040] Next, this specification is described in more detail.

[0041] The present invention provides an organic light-emitting device, which includes: an anode; a cathode; a light-emitting layer arranged between the anode and the cathode; a first organic layer arranged between the anode and the light-emitting layer and containing a compound of the following chemical formula 1; and a second organic layer arranged between the anode and the light-emitting layer and containing a compound of the following chemical formula 2.

[0042] In the present specification, examples of substituents are described below, but are not limited thereto.

[0043] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0044] In the present specification, the term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or is substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or has no substituent. For example, the "substituent formed by connecting two or more substituents" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, etc.

[0045] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, the number of carbon atoms is preferably 1 to 20. More specifically, the number of carbon atoms is preferably 1 to 10. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, 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-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0046] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and more preferably a cycloalkyl group having 3 to 20 carbon atoms. Specifically, there are 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 can be straight chain, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 30. Specifically, the preferred number of carbon atoms is 1 to 20. More specifically, the preferred number of carbon atoms is 1 to 10. Specifically, it can be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, an isopropyloxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, an n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but it is not limited thereto.

[0048] In the present specification, the amine group can be selected from -NH2, alkylamine, N-alkylarylamine, arylamine, N-arylheteroarylamine, N-alkylheteroarylamine and heteroarylamine, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthracenylamino, 9-methylanthrylamino, diphenylamino, N-phenylnaphthylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, and N-biphenylfluorenylamino.

[0049] In the present specification, the silyl group can be represented by the chemical formula -SiRaRbRc, wherein the above Ra, Rb and Rc are the same or different from each other and can be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group independently. The above silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto.

[0050] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms. The above aryl group may be monocyclic or polycyclic. When the above aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 6 to 30. More specifically, the number of carbon atoms is preferably 6 to 20. Specifically, as a monocyclic aryl group, phenyl, biphenyl, terphenyl, etc. may be mentioned, but are not limited thereto. When the above aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 10 to 30, and more specifically, the number of carbon atoms is preferably 10 to 20. Specifically, as a polycyclic aryl group, naphthyl, anthracenyl, phenanthrenyl, triphenyl, pyrenyl, phenanthrenyl, peryl, yl, fluorenyl, etc., but are not limited to these.

[0051] In this specification, "adjacent" groups may refer to substituents substituted on atoms directly connected to the atom substituted by the substituent, substituents closest to the substituent in stereostructure, or other substituents substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0052] 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 above-mentioned arylamine groups may be a monocyclic aryl group or a polycyclic aryl group. The arylamine groups containing two or more of the above-mentioned aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the above-mentioned arylamine groups may be selected from the examples of the above-mentioned aryl groups.

[0053] In the present specification, the heteroaryl group contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may contain one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 30, more preferably the number of carbon atoms is 2 to 20. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl 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, isothiophene Examples of the present invention include, but are not limited to, oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl.

[0054] In the present specification, the heterocyclic group contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms contain one or more atoms selected from O, N, Se, S, etc., including aromatic heterocyclic groups or aliphatic heterocyclic groups. The aromatic heterocyclic group can be represented by a heteroaryl group. An aliphatic heterocyclic group refers to a situation in which a heteroatom is contained in an aliphatic hydrocarbon ring such as tetrahydrofuran or pyrrolidine; or a heteroatom is contained in a ring in a form in which an aromatic and aliphatic ring are fused, such as isoindoline. The heteroaryl group is also included in the scope of the heterocyclic group. The number of carbon atoms in the heterocyclic group is not particularly limited, but preferably the number of carbon atoms is 2 to 30, more preferably the number of carbon atoms is 2 to 20, and the heteroaryl group can be a monocyclic or polycyclic ring.

[0055] In the present specification, a ring refers to an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring or a heterocyclic ring.

[0056] In the present specification, a hydrocarbon ring is a general term for a ring composed of carbon and hydrogen. The types of hydrocarbon rings include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, or hydrocarbon rings in which aliphatic and aromatic rings are condensed with each other, but are not limited thereto.

[0057] In the present specification, the aromatic hydrocarbon ring has the same definition as the aryl group except that it is not monovalent.

[0058] In this specification, the aliphatic hydrocarbon ring includes all hydrocarbon rings with single bonds, hydrocarbon rings containing multiple bonds, or rings containing single bonds and multiple bonds fused together. Therefore, the ring formed by a single bond in the aliphatic hydrocarbon ring includes the cycloalkyl group. Hydrocarbon rings containing single bonds and double bonds but not aromatic rings such as cyclohexene also belong to aliphatic hydrocarbon rings.

[0059] In the present specification, the heterocycle contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may contain one or more atoms selected from O, N, Se, S, etc. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic. The aromatic heterocycle may be selected from the examples of heteroaryl groups in the heterocyclic group except that it is not monovalent.

[0060] In the present specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, Examples of the present invention include, but are not limited to, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azacyclooctane, thiocane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran.

[0061] In the present specification, the above description about the aryl group is applicable to the arylene group except that the arylene group is a divalent group.

[0062] In the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4.

[0063] [Chemical formula 1-1]

[0064]

[0065] [Chemical formula 1-2]

[0066]

[0067] [Chemical formula 1-3]

[0068]

[0069] [Chemical formula 1-4]

[0070]

[0071] In the above Chemical Formulae 1-1 to 1-4, the definitions of R1, R2, L1 to L4, Ar1 to Ar3, a, b, and p to s are the same as those in Chemical Formula 1.

[0072] In this specification, the above Chemical Formula 2 is the following Chemical Formula 1-5 or 1-6.

[0073] [Chemical formula 1-5]

[0074]

[0075] [Chemical formula 1-6]

[0076]

[0077] In the above Chemical Formulae 1-5 and 1-6, the above R3 to R6, L5, Ar4, c to f and t are defined the same as those in Chemical Formula 2.

[0078] In this specification, the above Chemical Formula 2 is any one of the following Chemical Formulas 1-7 to 1-11.

[0079] [Chemical formula 1-7]

[0080]

[0081] [Chemical formula 1-8]

[0082]

[0083] [Chemical formula 1-9]

[0084]

[0085] [Chemical formula 1-10]

[0086]

[0087] [Chemical formula 1-11]

[0088]

[0089] In the above Chemical Formulae 1-7 to 1-11, the above R3 to R6, L5, Ar4, c to f and t are defined the same as those in Chemical Formula 2.

[0090] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0091] In one embodiment of the present specification, R1 and R2 are hydrogen.

[0092] In one embodiment of the present specification, R1 and R2 are deuterium.

[0093] In one embodiment of the present specification, R3 and R4 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0094] In one embodiment of the present specification, R3 and R4 are hydrogen.

[0095] In one embodiment of the present specification, R3 and R4 are deuterium.

[0096] In one embodiment of the present specification, R5 and R6 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.

[0097] In one embodiment of the present specification, R5 and R6 are the same as or different from each other, and are each independently hydrogen, deuterium, or an aryl group having 6 to 20 carbon atoms.

[0098] In one embodiment of the present specification, R5 and R6 are the same as or different from each other, and are each independently hydrogen, deuterium, or an aryl group having 6 to 18 carbon atoms.

[0099] In one embodiment of the present specification, R5 and R6 are the same as or different from each other, and are each independently hydrogen, deuterium, phenyl or naphthyl.

[0100] In one embodiment of the present specification, R5 and R6 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0101] In one embodiment of the present specification, R5 and R6 are the same as or different from each other, and are each independently a phenyl group or a naphthyl group.

[0102] In this specification, when p is 2 or more, it means that two or more L1 are sequentially bonded. For example, when p is 2, phenylene and naphthyl may be sequentially bonded and bonded to each other as shown below. In the following, the dotted line is the site bonded to other substituents or the core structure.

[0103]

[0104] In one embodiment of the present specification, the above-mentioned L1 is a direct bond.

[0105] In one embodiment of the present specification, the above-mentioned L2 is a direct bond or an arylene group having 6 to 30 carbon atoms.

[0106] In one embodiment of the present specification, the above-mentioned L2 is a direct bond or an arylene group having 6 to 20 carbon atoms.

[0107] In one embodiment of the present specification, the above-mentioned L2 is a direct bond, a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.

[0108] In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond or an arylene group having 6 to 30 carbon atoms.

[0109] In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond or an arylene group having 6 to 20 carbon atoms.

[0110] In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond or a phenylene group.

[0111] In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.

[0112] In one embodiment of the present specification, the above-mentioned L5 is a direct bond or an arylene group having 6 to 30 carbon atoms.

[0113] In one embodiment of the present specification, the above-mentioned L5 is a direct bond or an arylene group having 6 to 20 carbon atoms.

[0114] In one embodiment of the present specification, the above-mentioned L5 is a direct bond or an arylene group having 6 to 15 carbon atoms.

[0115] In one embodiment of the present specification, the above-mentioned L5 is a direct bond, a phenylene group, a divalent naphthyl group, or a divalent biphenylene group.

[0116] In one embodiment of the present specification, the above-mentioned L5 is a direct bond.

[0117] In one embodiment of the present specification, the above-mentioned L5 is a phenylene group, a divalent naphthyl group, or a divalent biphenylene group.

[0118] In one embodiment of the present specification, the Ar1 is an aryl group having 6 to 30 carbon atoms.

[0119] In one embodiment of the present specification, the Ar1 is an aryl group having 6 to 20 carbon atoms.

[0120] In one embodiment of the present specification, the Ar1 is an aryl group having 6 to 18 carbon atoms.

[0121] In one embodiment of the present specification, the Ar1 is a phenyl group, a biphenyl group or a naphthyl group.

[0122] In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently an aryl group which may be substituted or unsubstituted by an alkyl group or an aryl group, or a heteroaryl group.

[0123] In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms, which may be substituted or unsubstituted by an alkyl group or an aryl group.

[0124] In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently an aryl group having 6 to 24 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms, which is substituted or unsubstituted with an alkyl group or an aryl group.

[0125] In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently an aryl group having 6 to 24 carbon atoms, substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0126] In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently an aryl group having 6 to 24 carbon atoms, substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0127] In one embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and are each independently an aryl group having 6 to 24 carbon atoms, substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0128] In one embodiment of the present specification, the above-mentioned Ar2 and Ar3 are the same as or different from each other, and are each independently phenyl, biphenyl, naphthyl, terphenyl, triphenylene, spirobifluorenyl, fluorenyl substituted with methyl or phenyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl.

[0129] In one embodiment of the present specification, any one of Ar2 and Ar3 is a substituted or unsubstituted polycyclic aryl group, or a substituted or unsubstituted heteroaryl group.

[0130] In one embodiment of the present specification, any one of Ar2 and Ar3 is a naphthyl group, a triphenylene group, a spirobifluorenyl group, a fluorenyl group substituted with a methyl group or a phenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0131] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group, and A3 is a substituted or unsubstituted polycyclic aryl group, or a substituted or unsubstituted heteroaryl group.

[0132] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group, and Ar3 is a naphthyl group, a triphenylene group, a spirobifluorenyl group, a fluorenyl group substituted with a methyl group or a phenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0133] In one embodiment of the present specification, Ar4 is a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted cyclic group condensed therefrom.

[0134] In one embodiment of the present specification, Ar4 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a substituted or unsubstituted cyclic group formed by condensing these groups.

[0135] In one embodiment of the present specification, Ar4 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a substituted or unsubstituted cyclic group formed by condensing these groups.

[0136] In one embodiment of the present specification, Ar4 is phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, or tetrahydronaphthyl substituted with an alkyl group or an alkyl group.

[0137] In one embodiment of the present specification, Ar4 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothienyl, tert-butyl, substituted or unsubstituted with methyl or tert-butyl, or tetrahydronaphthyl, substituted or unsubstituted with methyl.

[0138] In one embodiment of the present specification, the above-mentioned Ar4 is a polycyclic aryl group.

[0139] In one embodiment of the present specification, Ar4 is a polycyclic aryl group having 10 to 20 carbon atoms.

[0140] In one embodiment of the present specification, the Ar4 is a naphthyl group or a phenanthrenyl group.

[0141] In one embodiment of the present specification, Ar4 is a cyclic group formed by condensing a cycloalkyl group having 10 to 20 carbon atoms and an aryl group.

[0142] In one embodiment of the present specification, the above-mentioned Ar4 is a tetrahydronaphthyl group substituted with a methyl group.

[0143] In one embodiment of the present specification, the Ar4 is a heteroaryl group having 3 to 30 carbon atoms.

[0144] In one embodiment of the present specification, Ar4 is a polycyclic heteroaryl group having 3 to 30 carbon atoms.

[0145] In one embodiment of the present specification, Ar4 is a dibenzofuranyl group or a dibenzothiophenyl group.

[0146] According to one embodiment of the present specification, the compound represented by the above Chemical Formula 1 is represented by any one of the following compounds.

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153] The above Dn-Dm indicates that the number of deuterium substituted in the compound in the brackets is n to m.

[0154] According to one embodiment of the present specification, the compound represented by the above Chemical Formula 2 is represented by any one of the following compounds.

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168] The above Dn-Dm indicates that the number of deuterium substituted in the compound in the brackets is n to m.

[0169] The substituents of the compounds of the above chemical formulas 1 and 2 may be combined by methods known in the art, and the type, position or number of the substituents may be changed according to techniques known in the art.

[0170] In addition, by introducing various substituents into the core structure of the structure shown above, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the above core structure, a material that meets the conditions required in each organic layer can be synthesized.

[0171] The organic light-emitting device of the present invention can be manufactured using conventional organic light-emitting device manufacturing methods and materials except that two or more organic layers are formed using the above-mentioned compound.

[0172] The above compounds can be formed into an organic layer by not only vacuum evaporation method but also solution coating method when manufacturing organic light-emitting devices. Here, the so-called solution coating method refers to spin coating method, dip coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0173] The organic layer of the organic light-emitting device of the present invention may be formed by a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers or a larger number of organic layers.

[0174] In the organic light-emitting device of the present invention, the above-mentioned organic layer may include an electron transport layer, an electron injection layer, and one or more layers of a layer that simultaneously performs electron injection and electron transport, and one or more of the above-mentioned layers may contain a compound represented by the above-mentioned Chemical Formula 1 or 2.

[0175] In another organic light-emitting device, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Chemical Formula 1 or 2.

[0176] In the organic light-emitting device of the present invention, the above-mentioned organic layer may include a hole injection layer, a hole transport layer, and one or more layers of a layer that simultaneously performs hole injection and hole transport, and one or more of the above-mentioned layers may contain the compound represented by the above-mentioned Chemical Formula 1 or 2.

[0177] In another organic light emitting device, the organic layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include the compound represented by Chemical Formula 1 or 2.

[0178] In one embodiment of the present specification, the second organic layer is located between the first organic layer and the light-emitting layer.

[0179] In one embodiment of the present specification, the first organic layer and the second organic layer are in contact with each other.

[0180] In one embodiment of the present specification, another layer is stacked between the first organic substance layer and the second organic substance layer.

[0181] In one embodiment of the present specification, the first organic layer is a first hole transport layer, and the second organic layer is a second hole transport layer.

[0182] (1) Anode / hole transport layer / light-emitting layer / cathode

[0183] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0184] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0185] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0186] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0187] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0188] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0189] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0190] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0191] (10) Anode / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / cathode

[0192] (11) Anode / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0193] (12) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / cathode

[0194] (13) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0195] (14) Anode / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / cathode

[0196] (15) Anode / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0197] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / cathode

[0198] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0199] (18) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / hole suppression layer / electron injection and transport layer / cathode

[0200] The structure of the organic light emitting device of the present invention may have the following Figure 1 and Figure 2 The structure shown is not limited thereto.

[0201] Figure 1 exemplifies the structure of an organic light-emitting device in which an anode 2, a first hole transport layer 3, a second hole transport layer 4, a light-emitting layer 5 and a second electrode 6 are sequentially stacked on a substrate 1.

[0202] Figure 2 exemplifies the structure of an organic light-emitting device in which an anode 2, a hole injection layer 7, a first hole transport layer 3, a second hole transport layer 4, a light-emitting layer 5, a hole suppression layer 8, an electron injection and transport layer 9, and a second electrode 6 are sequentially stacked on a substrate 1. In the structure shown above, the compound represented by the above chemical formula 1 may be contained in the first hole injection layer 3, and the compound represented by the above chemical formula 2 may be contained in the above second hole transport layer 4.

[0203] For example, the organic light-emitting device according to the present invention can be manufactured as follows: a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate by a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, and then an organic layer including one or more layers selected from a hole injection layer, a hole transport layer, a layer for simultaneously performing hole transport and hole injection, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer for simultaneously performing electron transport and electron injection is formed on the anode, and then a substance that can be used as a cathode is deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0204] In addition, the organic layer can be made of various polymer materials and manufactured into a smaller number of layers through a solvent process other than evaporation, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0205] The anode is an electrode for injecting holes. As the anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); 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, but are not limited thereto.

[0206] The cathode is an electrode for injecting electrons. In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. 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.

[0207] The hole injection layer is a layer that plays a role in making the injection of holes from the anode to the light-emitting layer smooth. The hole injection material is a material that can well receive holes from the anode at a low voltage. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrines, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline and polythiophene conductive polymers, but are not limited to this. The thickness of the hole injection layer can be 1 to 150nm. When the thickness of the hole injection layer is more than 1nm, it has the advantage of preventing the hole injection characteristics from being reduced. When it is less than 150nm, it has the advantage of preventing the driving voltage from rising when the thickness of the hole injection layer is too thick to improve the migration of holes.

[0208] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0209] [Chemical formula HI-1]

[0210]

[0211] In the above chemical formula HI-1,

[0212] At least one of X'1 to X'6 is N, and the others are CH,

[0213] R309 to R314 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0214] According to one embodiment of the present specification, X'1 to X'6 are N.

[0215] According to one embodiment of the present specification, R309 to R314 are nitrile groups.

[0216] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0217]

[0218] The hole transport layer can play a role in smoothing the transport of holes. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable. As specific examples, there are arylamine organic substances, conductive polymers, and block copolymers with both conjugated parts and non-conjugated parts, but are not limited to these.

[0219] A hole buffer layer may be further disposed between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

[0220] An electron suppression layer may be provided between the hole transport layer and the light emitting layer. The electron suppression layer may use the above-mentioned spiro compound or a material known in the technical field.

[0221] The above-mentioned light-emitting layer can emit red, green or blue light, and can be formed of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. As specific examples, there are 8-hydroxy-quinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Compounds of the oxazole, benzothiazole and benzimidazole series; poly(p-phenylene vinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0222] The main material of the light-emitting layer includes aromatic fused ring derivatives or heterocyclic compounds. Specifically, aromatic fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0223] According to one embodiment of the present specification, the host includes a compound represented by the following chemical formula H-1, but is not limited thereto.

[0224] [Chemical formula H-1]

[0225]

[0226] In the above chemical formula H-1,

[0227] L20 and L21 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0228] Ar20 and Ar21 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0229] R201 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0230] r201 is an integer of 1 to 8. When r201 is 2 or more, two or more R201s are the same as or different from each other.

[0231] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond, a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0232] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond, a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group, a deuterium-substituted or unsubstituted naphthylene group, a divalent dibenzofuranyl group, or a divalent dibenzothiophenyl group.

[0233] In one embodiment of the present specification, the Ar20 is a substituted or unsubstituted heterocyclic group, and the Ar21 is a substituted or unsubstituted aryl group.

[0234] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0235] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0236] In one embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and are each independently substituted or unsubstituted phenyl by deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; biphenyl by deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthyl by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Thienyl substituted or unsubstituted by aryl; dibenzofuranyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthobenzofuranyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; dibenzothienyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or naphthobenzothienyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0237] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted by deuterium, a biphenyl group substituted or unsubstituted by deuterium, a terphenyl group, a naphthyl group substituted or unsubstituted by deuterium, a thienyl group substituted or unsubstituted by phenyl, a phenanthryl group, a dibenzofuranyl group, a naphthiobenzofuranyl group, a dibenzothiophenyl group or a naphthiobenzothiophenyl group.

[0238] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently 1-naphthyl or 2-naphthyl.

[0239] According to one embodiment of the present specification, the above R201 is hydrogen.

[0240] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0241]

[0242] When the light-emitting layer emits red light, as a light-emitting dopant, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium, bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium, bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium, tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the light-emitting layer emits green light, as a light-emitting dopant, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium, face tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinoline)aluminum) can be used, but it is not limited to these. When the light-emitting layer emits blue light, as a light-emitting dopant, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used; or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers can be used, but it is not limited to these.

[0243] According to one embodiment of the present specification, the dopant includes a compound represented by the following Chemical Formula D-1, but is not limited thereto.

[0244] [Chemical formula D-1]

[0245]

[0246] In the above chemical formula D-1,

[0247] T1 to T6 are the same as or different from each other, and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0248] t5 and t6 are each an integer from 1 to 4,

[0249] When the above t5 is 2 or more, the above two or more T5 are the same or different from each other.

[0250] When the above t6 is 2 or more, the above two or more T6 may be the same as or different from each other.

[0251] According to one embodiment of the present specification, the above-mentioned T1 to T6 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0252] According to one embodiment of the present specification, the above-mentioned T1 to T6 are the same as or different from each other and are independently hydrogen; a straight-chain or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted by a nitrile group or a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is unsubstituted or substituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0253] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently hydrogen, a phenyl group which may be substituted with a methyl group, or a dibenzofuranyl group which is substituted with a terphenyl group.

[0254] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0255]

[0256] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the technical field may be used.

[0257] According to one embodiment of the present specification, the hole suppression layer includes a compound of the following chemical formula HB-1.

[0258] [Chemical formula HB-1]

[0259]

[0260] In the above chemical formula HB-1,

[0261] At least one of Z1 to Z3 is N, and the others are CH,

[0262] L601 and L602 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0263] Ar601 to Ar603 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0264] According to one embodiment of the present specification, the above L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0265] According to one embodiment of the present specification, L601 and L602 are the same as or different from each other, and are each independently a phenylene group, a biphenylene group, or a naphthylene group.

[0266] According to one embodiment of the present specification, Ar601 to Ar603 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0267] According to one embodiment of the present specification, Ar601 to Ar603 are phenyl groups or triphenylene groups.

[0268] According to one embodiment of the present specification, the chemical formula HB-1 is represented by the following compound.

[0269]

[0270] The above-mentioned electron transport layer can play a role in making the transmission of electrons smooth. The electron transport material is a material that can receive electrons well from the cathode and transfer them to the light-emitting layer, and is suitable for materials with high electron mobility. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. The thickness of the electron transport layer can be 1 to 50nm. When the thickness of the electron transport layer is more than 1nm, it has the advantage of preventing the electron transport characteristics from being reduced. When it is less than 50nm, it has the advantage of preventing the driving voltage from rising in order to improve the migration of electrons when the thickness of the electron transport layer is too thick.

[0271] The electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferred: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0272] The electron injection and transport layer is a layer that facilitates the injection and transport of electrons. The materials used in the electron injection and transport layers mentioned above or materials that can smoothly receive electrons from the cathode and transfer them to the light-emitting layer can be used.

[0273] According to one embodiment of the present specification, the electron injection and transport layer includes a compound of the following chemical formula EI-1.

[0274] [Chemical formula EI-1]

[0275]

[0276] In the above chemical formula EI-1,

[0277] At least one of Z11 to Z13 is N, and the rest are CH,

[0278] At least one of Z14 to Z16 is N, and the rest are CH,

[0279] L701 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0280] Ar701 to Ar704 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0281] l701 is an integer from 1 to 4. When l701 is a plural number, L701 are the same as or different from each other.

[0282] According to one embodiment of the present specification, the above L701 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0283] According to one embodiment of the present specification, the L701 is a phenylene group, a biphenylene group, or a naphthylene group.

[0284] According to one embodiment of the present specification, the above-mentioned L701 is a phenylene group or a naphthylene group.

[0285] According to one embodiment of the present specification, Ar701 to Ar704 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0286] According to one embodiment of the present specification, Ar701 to Ar704 are phenyl groups.

[0287] According to one embodiment of the present specification, the chemical formula HB-1 is represented by the following compound.

[0288]

[0289] Examples of the metal coordination compounds include, but are not limited to, 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, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0290] The hole blocking layer is a layer that prevents holes from reaching the cathode and can usually be formed using the same conditions as the electron injection layer. Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0291] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0292] The organic light-emitting device of the present invention uses the above-mentioned compound to form one or more organic layers, and can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0293] The methods for preparing the compounds of the above chemical formulas 1 and 2 and the preparation of an organic light-emitting device using the same are specifically described in the following examples. However, the following examples are used to illustrate the present invention, and the scope of the present invention is not limited thereto.

[0294] Modes for Carrying Out the Invention

[0295] In the following reaction formula, the type and number of substituents can be appropriately selected by a person skilled in the art from known starting materials to synthesize various types of intermediates. The type and conditions of the reaction can be determined by techniques known in the art.

[0296] All the compounds of the above Chemical Formulae 1 and 2 described in the present specification can be produced by appropriately combining the production formulae described in the Examples of the present specification and the above intermediates based on common technical knowledge.

[0297] <Synthesis Example of Chemical Formula 1>

[0298] Synthesis Example A-1. Synthesis of Compound A-1

[0299]

[0300] Toluene (150 ml) was added to 3-(4-chlorophenyl)-9-phenyl-9H-carbazole (20.0 g, 56.52 mmol), di([1,1'-biphenyl]-4-yl)amine (18.53 g, 57.65 mmol) and sodium tert-butoxide (7.60 g, 79.13 mmol), and the mixture was heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.14 g, 0.28 mmol) dissolved in toluene (10 ml) was added to the above mixture, and the mixture was heated and stirred for 1 hour. After the reaction was completed and filtered, the layers were separated with toluene and water. After removing the solvent, the mixture was recrystallized with ethyl acetate to obtain the above compound A-1 (28.5 g, 78.94% yield). (MS[M+H] + =639)

[0301] Synthesis Example A-2. Synthesis of Compound A-2

[0302]

[0303] Using 3-(4-chlorophenyl)-9-phenyl-9H-carbazole (20.0 g, 56.52 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine (22.92 g, 57.65 mmol), the above-mentioned compound A-2 (32.0 g, 79.19% yield) was obtained by the same method as the above-mentioned Synthesis Example A-1. (MS [M+H] + =715)

[0304] Synthesis Example A-3. Synthesis of Compound A-3

[0305]

[0306] Using 3-(4-chlorophenyl)-9-phenyl-9H-carbazole (20.0 g, 56.52 mmol) and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (20.84 g, 57.65 mmol), the above-mentioned compound A-3 (32.0 g, 79.19% yield) was obtained by the same method as the above-mentioned Synthesis Example A-1. (MS [M+H] + =679)

[0307] Synthesis Example A-4. Synthesis of Compound A-4

[0308]

[0309] Using 3-(4'-chloro-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-carbazole (20.0 g, 46.52 mmol) and di([1,1'-biphenyl]-4-yl)amine (15.25 g, 47.45 mmol), the above-mentioned compound A-4 (26.0 g, 78.18% yield) was obtained by the same method as the above-mentioned Synthesis Example A-1. (MS[M+H] + =715)

[0310] Synthesis Example A-5. Synthesis of Compound A-5

[0311]

[0312] Using 3-(4-chlorophenyl)-9-(naphthalen-2-yl)-9H-carbazole (20.0 g, 49.52 mmol) and di([1,1'-biphenyl]-4-yl)amine (16.23 g, 50.51 mmol), the above-mentioned compound A-5 (27.0 g, 79.15% yield) was obtained by the same method as the above-mentioned synthesis example A-1. (MS [M+H] + =689)

[0313] Synthesis Example A-6. Synthesis of Compound A-6

[0314]

[0315] Using 3-(4-chlorophenyl)-9-(naphthalene-2-yl)-9H-carbazole (20.0 g, 49.52 mmol) and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (18.26 g, 50.51 mmol), the above-mentioned compound A-6 (28.5 g, 78.95% yield) was obtained by the same method as the above-mentioned synthesis example A-1. (MS [M+H] + =729)

[0316] Synthesis Example A-7. Synthesis of Compound A-7

[0317]

[0318] In the above-mentioned synthesis example A-1, the obtained compound A-1 (20.0 g, 31.31 mmol) was added to benzene-d6 (200 ml), and after complete dissolution, trifluoromethanesulfonic acid (1.4 ml, 15.65 mmol) was added and stirred for 25 minutes. After the reaction was completed, dichloromethane was added and the layers were separated to obtain an organic layer. After drying with anhydrous magnesium sulfate (MgSO4), it was filtered. The filtrate was concentrated under reduced pressure and recrystallized with ethyl acetate to obtain the above-mentioned compound A-7 (16.0 g, 76.73%). (MS[M+H] + =666)

[0319] Synthesis Example A-8. Synthesis of Compound A-8

[0320]

[0321] Using the compound A-3 (20.0 g, 29.46 mmol) obtained in the above-mentioned synthesis example A-3, the above-mentioned compound A-8 (16.5 g, 79.55% yield) was obtained by the same method as the above-mentioned synthesis example A-7. (MS [M+H] + =704)

[0322] Synthesis Example B-1. Synthesis of Compound B-1

[0323]

[0324] Toluene (150 ml) was added to 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-carbazole (20.0 g, 56.52 mmol), N-(3-(naphthalen-1-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine (25.80 g, 57.65 mmol) and sodium tert-butoxide (7.60 g, 79.13 mmol), and the mixture was heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.15 g, 0.28 mmol) dissolved in toluene (10 ml) was added to the above mixture, and the mixture was heated and stirred for 1 hour. After the reaction was completed and filtered, the layers were separated with toluene and water. After removing the solvent, the mixture was recrystallized with ethyl acetate to obtain the above compound B-1 (34.0 g, 78.64% yield). (MS[M+H] + =765)

[0325] Synthesis Example B-2. Synthesis of Compound B-2

[0326]

[0327] Using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-carbazole (20.0 g, 56.52 mmol) and 3-(naphthalene-1-yl)-N-(4-(naphthalene-1-yl)phenyl)aniline (24.30 g, 57.65 mmol), the above-mentioned compound B-2 (33.5 g, 80.21% yield) was obtained by the same method as the above-mentioned synthesis example B-1. (MS [M+H] + =739)

[0328] Synthesis Example B-3. Synthesis of Compound B-3

[0329]

[0330] The above-mentioned compound B-3 (33.0 g, 79.01% yield) was obtained by the same method as the above-mentioned synthesis example B-1 using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-carbazole (20.0 g, 56.52 mmol) and bis(3-(naphthalen-1-yl)phenyl)amine (24.30 g, 57.65 mmol). (MS[M+H] + =739)

[0331] Synthesis Example B-4. Synthesis of Compound B-4

[0332]

[0333] Using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-carbazole (20.0 g, 56.52 mmol) and 3-(naphthalene-2-yl)-N-(4-(naphthalene-2-yl)phenyl)aniline (24.30 g, 57.65 mmol), the above-mentioned compound B-4 (33.0 g, 79.01% yield) was obtained by the same method as the above-mentioned synthesis example B-1. (MS [M+H] + =739)

[0334] Synthesis Example B-5. Synthesis of Compound B-5

[0335]

[0336] Using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-carbazole (20.0 g, 56.52 mmol) and N-(3-(naphthalen-1-yl)phenyl)-4-phenylnaphthyl-1-amine (24.30 g, 57.65 mmol), the above-mentioned compound B-5 (32.5 g, 77.82% yield) was obtained by the same method as the above-mentioned synthesis example B-1. (MS [M+H] + =739)

[0337] Synthesis Example B-6. Synthesis of Compound B-6

[0338]

[0339] Using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-carbazole (20.0 g, 56.52 mmol) and N-(3-(phenanthrene-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (24.30 g, 57.65 mmol), the above-mentioned compound B-6 (33.0 g, 79.01% yield) was obtained by the same method as the above-mentioned synthesis example B-1. (MS [M+H] + =739)

[0340] Synthesis Example B-7. Synthesis of Compound B-7

[0341]

[0342] Using 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-carbazole (20.0 g, 56.52 mmol) and N-(3-(phenanthrene-9-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine (28.69 g, 57.65 mmol), the above-mentioned compound B-7 (36.5 g, 79.24% yield) was obtained by the same method as the above-mentioned synthesis example B-1. (MS [M+H] + =815)

[0343] Synthesis Example B-8. Synthesis of Compound B-8

[0344]

[0345] The above-mentioned compound B-8 (27.5 g, 77.28% yield) was obtained by the same method as the above-mentioned synthesis example B-1 using 9-(4'-chloro-[1,1':3',1"-terphenyl]-2-yl)-9H-carbazole (20.0 g, 46.52 mmol) and N-(3-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol). (MS [M+H] + =765)

[0346] Synthesis Example B-9. Synthesis of Compound B-9

[0347]

[0348] Using 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9H-carbazole (20.0 g, 46.52 mmol) and N-(3-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), the above-mentioned compound B-9 (28.5 g, 80.09% yield) was obtained by the same method as the above-mentioned synthesis example B-1. (MS [M+H] + =765)

[0349] Synthesis Example B-10. Synthesis of Compound B-10

[0350]

[0351] Using 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9H-carbazole (20.0 g, 46.52 mmol) and N-(3-(phenanthrene-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (20.00 g, 47.45 mmol), the above-mentioned compound B-10 (30.0 g, 79.12% yield) was obtained by the same method as the above-mentioned Synthesis Example B-1. (MS [M+H] + =815)

[0352] Synthesis Example B-11. Synthesis of Compound B-11

[0353]

[0354] Using the compound B-2 (20.0 g, 27.07 mmol) obtained in the above-mentioned synthesis example B-2, the above-mentioned compound B-11 (16.5 g, 79.25% yield) was obtained by the same method as the above-mentioned synthesis example A-7. (MS [M+H] + =769)

[0355] Synthesis Example B-12. Synthesis of Compound B-12

[0356]

[0357] Using the compound B-6 (20.0 g, 27.07 mmol) obtained in the above-mentioned synthesis example B-6, the above-mentioned compound B-12 (16.5 g, 79.25% yield) was obtained by the same method as the above-mentioned synthesis example A-7. (MS [M+H] + =769)

[0358] <Experimental Examples and Comparative Experimental Examples>

[0359] Experimental Example 1

[0360] ITO (indium tin oxide) The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0361] On the ITO transparent electrode prepared in this way, a compound represented by the following chemical formula HAT was applied as On the hole injection layer, as a first hole transport layer, the compound A-1 prepared in the above-mentioned synthesis example A-1 was prepared in the above-mentioned manner. After vacuum deposition with a thickness of , as the second hole transport layer, the compound B-1 prepared in the above-mentioned synthesis example B-1 was Next, as a light-emitting layer, a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were added at a weight ratio of 50:1 and at a weight ratio of Next, as a hole suppression layer, a compound represented by the following chemical formula HB was deposited in an amount of Next, as an electron injection and transport layer, a compound represented by the following chemical formula ET and a compound represented by the following Liq were added at a weight ratio of 1:1 and at a thickness of On the electron injection and transport layer, lithium fluoride (LiF) is deposited in the form of The thickness of the aluminum A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.

[0362]

[0363] Experimental Examples 2 to 66 and Comparative Examples 1 to 40

[0364] In the above Experimental Example 1, the organic light-emitting devices of Experimental Examples 2 to 66 and Comparative Examples 1 to 40 were prepared by the same method as in the above Experimental Example 1, except that the compounds described in the following Table 1 were used instead of Compound A-1 as the first hole transport layer, and the compounds described in the following Table 1 were used instead of Compound B-1 as the second hole transport layer. The organic light-emitting devices prepared in the Experimental Examples and Comparative Examples were subjected to a 10 mA / cm 2The voltage, efficiency, color coordinates and life were measured when the current was 1.0 0.05 0.05 0.06 0.06 0.08 ...

[0365] [Table 1]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372] As shown in Table 1, it is confirmed that the organic light-emitting device of the present invention using the compound represented by Chemical Formula 1 as the first hole transport layer and the compound represented by Chemical Formula 2 as the second hole transport layer shows significant effects in terms of driving voltage, efficiency and lifespan.

[0373] Comparative Examples 1 to 4 include only any one of the layer containing the compound of the above Chemical Formula 1 and the layer containing the compound of the above Chemical Formula 2.

[0374] Comparative Examples 5 to 20 are different from the compounds of Chemical Formula 2 of the present invention in that they do not include a naphthyl group or a phenanthryl group bonded to an amine group in a meta-position.

[0375] Comparative Examples 21 to 36 are different from the compounds of Chemical Formula 1 of the present invention in that one of Ar2 and Ar3 is a hexacyclic aryl group or a substituent formed by condensing an aryl group with a cycloalkyl group.

[0376] Comparative Examples 37 to 40 did not use both the compound of Chemical Formula 1 and the compound of Chemical Formula 2 of the present invention.

[0377] It can be confirmed that Examples 1 to 103 have the effects of low voltage, high efficiency, and long life compared with Comparative Examples 1 to 40.

[0378] As shown in Table 1, it is confirmed that the organic light-emitting device of the present invention using the compound represented by Chemical Formula 1 as the first hole transport layer and the compound represented by Chemical Formula 2 as the second hole transport layer shows significant effects in terms of driving voltage, efficiency and lifespan.

Claims

1. An organic light-emitting device, wherein: include: anode; cathode; A light-emitting layer disposed between the anode and the cathode; A first organic layer disposed between the anode and the light-emitting layer and comprising a compound of the following Chemical Formula 1; as well as A second organic layer is provided between the anode and the light-emitting layer and includes a compound of the following Chemical Formula 2: [Chemical formula 1] [Chemical formula 2] In the chemical formulas 1 and 2, Ar1 is a substituted or unsubstituted aryl group, Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted heteroaryl group, Ar4 is a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring formed by condensing these groups. Ar5 is unsubstituted naphthyl or unsubstituted phenanthrenyl, R1 to R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R5 and R6 are the same or different from each other and are each independently hydrogen, deuterium or aryl, L1 to L5 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group, a and c to f are integers from 0 to 4, b is an integer from 0 to 3, When a to f are 2 or more, R1 to R6 are the same as or different from each other. p, q, r, s and t are each an integer from 0 to 2, When p to t are 2 or more, L1 to L5 are the same as or different from each other.

2. The organic light emitting device according to claim 1, wherein: The chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] In the Chemical Formulae 1-1 to 1-4, the definitions of R1, R2, L1 to L4, Ar1 to Ar3, a, b, and p to s are the same as those in Chemical Formula 1.

3. The organic light emitting device according to claim 1, wherein: The chemical formula 2 is represented by the following chemical formula 1-5 or 1-6: [Chemical formula 1-5] [Chemical formula 1-6] In the Chemical Formulas 1-5 and 1-6, the definitions of R3 to R6, L5, Ar4, c to f and t are the same as those in Chemical Formula 2.

4. The organic light emitting device according to claim 1, wherein: The chemical formula 2 is represented by any one of the following chemical formulas 1-7 to 1-11: [Chemical formula 1-7] [Chemical formula 1-8] [Chemical formula 1-9] [Chemical formula 1-10] [Chemical formula 1-11] In the Chemical Formulae 1-7 to 1-11, the definitions of R3 to R6, L5, Ar4, c to f and t are the same as those in Chemical Formula 2.

5. The organic light emitting device according to claim 1, wherein: The R5 and R6 are the same as or different from each other, and are independently phenyl or naphthyl.

6. The organic light emitting device according to claim 1, wherein: The R5 and R6 are hydrogen.

7. The organic light emitting device according to claim 1, wherein: The Ar1 is phenyl, naphthyl or biphenyl.

8. The organic light emitting device according to claim 1, wherein: Ar2 is a substituted or unsubstituted phenyl group, and A3 is a substituted or unsubstituted polycyclic aryl group, or a substituted or unsubstituted heteroaryl group.

9. The organic light emitting device according to claim 1, wherein: The chemical formula 1 is any one of the following compounds: The Dn-Dm indicates that the number of deuterium substituted in the compound in the brackets is n to m.

10. The organic light emitting device according to claim 1, wherein: The chemical formula 2 is any one of the following compounds: The Dn-Dm indicates that the number of deuterium substituted in the compound in the brackets is n to m.

11. The organic light emitting device according to claim 1, wherein: The second organic layer is located between the first organic layer and the light-emitting layer.

12. The organic light emitting device according to claim 1, wherein: The first organic layer and the second organic layer are connected to each other.

13. The organic light emitting device according to claim 1, wherein: Another layer is stacked between the first organic layer and the second organic layer.

14. The organic light emitting device according to claim 1, wherein: The first organic layer is a first hole transport layer, and the second organic layer is a second hole transport layer.

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