Organic light emitting device

Abstract

The present specification relates to an organic light-emitting device comprising a first electrode, a second electrode provided so as to face the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, the organic material layers including a light-emitting layer, the light-emitting layer includes a first host compound represented by Chemical Formula 1 or 2, a second host compound represented by Chemical Formula 3, a first dopant (phosphorescent) compound represented by Chemical Formula 4 or 5, and a second dopant (fluorescent) compound represented by Chemical Formula 6.

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2023-0057299, filed with the Korean Patent Office on May 2, 2023, the entire contents of which are contained in this specification.

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

[0003] Organic light emission (OLED) typically refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices generally have a structure comprising an anode and a cathode, with an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials; for example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, they form excitons. When these excitons re-enter the ground state, they emit light.

[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 manual provides information on organic light-emitting devices.

[0007] Solution to the problem

[0008] The present invention provides an organic light-emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode.

[0009] The aforementioned organic layer includes a light-emitting layer comprising a first host compound represented by chemical formula 1 or 2, a second host compound represented by chemical formula 3, a first dopant compound represented by chemical formula 4 or 5, and a second dopant compound represented by chemical formula 6.

[0010] [Chemical Formula 1]

[0011]

[0012] [Chemical Formula 2]

[0013]

[0014] In the above chemical formulas 1 and 2,

[0015] R1 to R6 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0016] R1 to R3 and L1 can combine with adjacent substituents to form a ring.

[0017] R4 to R6 and L2 can combine with adjacent substituents to form a ring.

[0018] R21 to R24 may be the same as or different from each other, and each is independently a hydrogen, deuterium, nitrile, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0019] R25 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0020] L1 and L2 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0021] a1 is an integer from 1 to 8.

[0022] a2 to a4 are each integers from 1 to 7.

[0023] When each of a1 to a4 has more than 2 substituents, the substituents within the parentheses may be the same or different from each other.

[0024] [Chemical Formula 3]

[0025]

[0026] In the above chemical formula 3,

[0027] X1 to X3 may be the same as or different from each other, and each can be N or CR independently.

[0028] R can be hydrogen, deuterium, nitrile, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkenyl, or substituted or unsubstituted heteroaryl.

[0029] HET is a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted heteroaryl group.

[0030] R7 to R9 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0031] R26 is hydrogen, deuterium, nitrile, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0032] When a6 is an integer from 1 to 8, and a6 is 2 or higher, R26 may be the same or different from each other.

[0033] L3 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0034] [Chemical Formula 4]

[0035]

[0036] [Chemical Formula 5]

[0037]

[0038] In the above chemical formulas 4 and 5,

[0039] M is a transition metal.

[0040] Z1 is a substituted or unsubstituted N-containing monocyclic or bicyclic heterocycle.

[0041] R11 and R12 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0042] R13 to R16, R18 to R20, and R35 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, nitrile, halogen, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted boryl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0043] a, b, and f are each integers from 1 to 3.

[0044] c, d, g, and h are each integers from 1 to 4.

[0045] a5 is 1 or 2.

[0046] When a to d and f to h are complex numbers, the substituents within the parentheses may be the same or different from each other.

[0047] When a5 is 2, R35 may be the same or different from each other.

[0048] [Chemical Formula 6]

[0049]

[0050] In the above chemical formula 6,

[0051] A1 to A3 may be the same as or different from each other, and each may be an independently substituted or unsubstituted heterocycle or a substituted or unsubstituted hydrocarbon ring.

[0052] B1 and B2 may be the same as or different from each other, and each may be a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted hydrocarbon cyclic group.

[0053] Invention Effects

[0054] The bulky silyl groups in the compounds represented by formulas 1 to 3 included in this specification participate in the conjugation system through a hyperconjugation effect, thereby possessing structural features that stabilize the excited and polaronic states. Furthermore, by using compounds represented by formulas 4 to 6, luminescence is induced through the Foster energy transfer process to the singlet state, reducing the stress on the nonradiative triplet state, thereby improving efficiency and lifetime. In particular, the aforementioned formula 6, with its narrow half-width, exhibits high color purity when incorporated into the organic layer of the organic light-emitting device. Attached Figure Description

[0055] Figure 1 An organic light-emitting device according to one embodiment of this specification is illustrated.

[0056] Figure 2 An organic light-emitting device according to one embodiment of this specification is illustrated.

[0057] [Symbol Explanation]

[0058] 1: Substrate

[0059] 2: Anode

[0060] 3: Organic layer

[0061] 4: Cathode

[0062] 5: Hole injection layer

[0063] 6: Hole transport layer

[0064] 7: Electron blocking layer

[0065] 8: Emissive layer

[0066] 9: Hole-blocking layer

[0067] 10: Electron Injection and Transport Layer Detailed Implementation

[0068] The following is a more detailed explanation of the contents of this book.

[0069]

[0070] The energy transfer process is illustrated in the table above. The host molecule, containing both singlet and triplet excitons, is excited and then induced to transfer energy to the phosphor via the Foster and Dexter energy transfer processes. The phosphor's singlet state can be transformed into a triplet state through the ISC process (black line). Finally, the phosphor's triplet state generates a large number of singlet excitons for the fluorescent emitter via the Foster energy transfer process (purple line). This is because the fluorescent emitter has a low doping concentration, and due to the spatial separation between the phosphor and the emitter, the energy transfer process to the emitter is dominated by the Foster energy transfer process. Therefore, compared to the case without a phosphor or fluorescent emitter, the generation of triplet states accumulated due to the Dexter energy transfer (blue line) is reduced, resulting in improved device efficiency and lifetime.

[0071] Examples of substituents in this specification are described below, but are not limited thereto.

[0072] The term "substitution" refers to the replacement of hydrogen atoms on carbon atoms in a compound with other substituents. There is no limitation on the position of substitution, as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0073] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, nitrile, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted alkoxy, substituted or unsubstituted arylamino, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic, or substituted by a substituent formed by linking two or more substituents exemplified above, or without any substituents. For example, "a substituent formed by linking two or more substituents" can 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.

[0074] In this specification, alkyl groups can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, it is preferred that the number of carbon atoms is 1 to 20. More specifically, it is preferred that the number of carbon atoms is 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, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0075] In this specification, cycloalkyl groups are not particularly limited, but are preferably cycloalkyl groups with 3 to 30 carbon atoms, and more preferably cycloalkyl groups with 3 to 20 carbon atoms. Specifically, they include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited to these.

[0076] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably 1 to 30. Specifically, 1 to 20 carbon atoms are preferred. More specifically, 1 to 10 carbon atoms are preferred. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited to these.

[0077] In this specification, the amino group may be selected from -NH2, alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino and heteroarylamino, 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, anthraceneamino, 9-methylanthraylamino, diphenylamino, N-phenylnaphthylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthreneamino, N-biphenylphenanthreneamino, N-phenylfluorenylamino, N-phenyltriphenylamino, N-phenanthrenefluorenylamino, N-biphenylfluorenylamino, etc., but are not limited to these.

[0078] In this specification, silyl groups can be represented by the chemical formula -SiRaRbRc, where Ra, Rb, and Rc may be the same or different from each other, and each can independently be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited to these.

[0079] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 30 carbon atoms, more preferably an aryl group with 6 to 20 carbon atoms. The aforementioned aryl group can be monocyclic or polycyclic. When the aforementioned aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. More specifically, the number of carbon atoms is preferably 6 to 20. Specifically, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. When the aforementioned aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30, more specifically, the number of carbon atoms is preferably 10 to 20. Specifically, as a polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, triphenyl, pyrene, beryl, perylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0080] In this specification, "adjacent" groups can refer to substituents that are directly bonded to the atom substituted by the substituent, substituents that are stereomorphically closest to the substituent, or other substituents that are substituted to the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon atom in an aliphatic ring can be interpreted as "adjacent" groups.

[0081] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, and substituted or unsubstituted triarylamine groups. The aryl group in the above-described arylamine group can be a monocyclic aryl group or a polycyclic aryl group. An arylamine group containing two or more of the above-described aryl groups can contain monocyclic aryl groups, polycyclic aryl groups, or both. For example, the aryl group in the above-described arylamine group can be selected from the examples of the aryl groups described above.

[0082] In this specification, a heteroaryl group comprises one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may comprise one or more atoms selected from O, N, Se, and S. The number of carbon atoms is not particularly limited, but preferably 2 to 30, more preferably 2 to 20. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thienyl, furanyl, pyrroleyl, imidazolyl, and thiazolyl. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, iso The group can be azole, thiadiazole, phenothiazinyl, or dibenzofuranyl, but is not limited to these.

[0083] In this specification, "ring" refers to a hydrocarbon ring, an aromatic ring, or a heterocycle.

[0084] In this specification, the hydrocarbon ring is defined the same as the cycloalkyl group, except that it is not a monovalent group.

[0085] In this specification, aromatic rings are defined the same as aryl groups, except that they are not monovalent groups.

[0086] In this specification, "ring" refers to an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, or a heterocycle.

[0087] In this specification, hydrocarbon rings are a general term for rings composed of carbon and hydrogen. Hydrocarbon rings include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, or hydrocarbon rings in which aliphatic and aromatic compounds are fused together, but are not limited to these types.

[0088] In this specification, the aromatic hydrocarbon rings described above are defined the same as those of the aryl groups described above, except that they are not monovalent.

[0089] In this specification, the term "aliphatic hydrocarbon ring" encompasses all hydrocarbon rings with single bonds, hydrocarbon rings containing double bonds, and rings in the form of fused single and double bonds. Therefore, aliphatic hydrocarbon rings formed by single bonds include the aforementioned cycloalkyl groups. Hydrocarbon rings containing single and double bonds, but not aromatic rings, such as cyclohexene, also belong to aliphatic hydrocarbon rings.

[0090] In this specification, a heterocycle comprises one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may comprise one or more atoms selected from O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic compounds. The aromatic heterocycles, except that they are not monovalent, may be selected from examples of heteroaryl groups among the aforementioned heterocyclic groups.

[0091] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, and 1,4-dioxane. Alkane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxacycloheptane, azirrocyclooctane, thiocyclooctane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran, etc., but not limited to these.

[0092] In this specification, the aliphatic hydrocarbon cyclic group is the same as the aliphatic hydrocarbon ring as defined above, except that it is monovalent.

[0093] In this specification, the above description of heteroaryl groups applies, except that the heteroaryl group is a divalent group.

[0094] In this specification, except that arylene is a divalent group, the above description of aryl groups applies.

[0095] In this specification, the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-4.

[0096] [Chemical Formula 1-1]

[0097]

[0098] [Chemical Formula 1-2]

[0099]

[0100] [Chemical Formulas 1-3]

[0101]

[0102] [Chemical Formulas 1-4]

[0103]

[0104] In the above chemical formulas 1-1 to 1-4, the definitions of R1 to R3, L1, R21, R22, a1, and a2 are the same as those in chemical formula 1.

[0105] In this specification, the above chemical formula 2 is any one of the following chemical formulas 2-1 to 2-16.

[0106] [Chemical Formula 2-1]

[0107]

[0108] [Chemical Formula 2-2]

[0109]

[0110] [Chemical Formula 2-3]

[0111]

[0112] [Chemical Formula 2-4]

[0113]

[0114] [Chemical Formula 2-5]

[0115]

[0116] [Chemical Formula 2-6]

[0117]

[0118] [Chemical Formula 2-7]

[0119]

[0120] [Chemical Formula 2-8]

[0121]

[0122] [Chemical Formula 2-9]

[0123]

[0124] [Chemical Formula 2-10]

[0125]

[0126] [Chemical Formula 2-11]

[0127]

[0128] [Chemical Formula 2-12]

[0129]

[0130] [Chemical Formula 2-13]

[0131]

[0132] [Chemical Formula 2-14]

[0133]

[0134] [Chemical Formula 2-15]

[0135]

[0136] [Chemical Formula 2-16]

[0137]

[0138] In the above chemical formulas 2-1 to 2-16, the definitions of R4 to R6, L2, R23 to R25, a3 and a4 are the same as those in chemical formula 2.

[0139] In this specification, R1 to R6 may be the same as or different from each other, and each is independently an alkyl group substituted with or unsubstituted with deuterium, or an aryl group substituted with or unsubstituted with deuterium.

[0140] In this specification, R1 to R6 may be the same as or different from each other, and each is independently an alkyl group with 1 to 10 carbon atoms that is substituted with deuterium or unsubstituted, or an aryl group with 6 to 30 carbon atoms that is substituted with deuterium or unsubstituted.

[0141] In this specification, R1 to R6 may be the same as or different from each other, and each is independently an alkyl group having 1 to 7 carbon atoms that is substituted with deuterium or not substituted, or an aryl group having 6 to 20 carbon atoms that is substituted with deuterium or not substituted.

[0142] In this specification, R1 to R6 may be the same as or different from each other, and each is independently an alkyl group having 1 to 5 carbon atoms that is substituted with deuterium or not substituted, or an aryl group having 6 to 15 carbon atoms that is substituted with deuterium or not substituted.

[0143] In this specification, R1 to R6 may be the same as or different from each other, and each independently represents a methyl group that is substituted or unsubstituted with deuterium, an ethyl group that is substituted or unsubstituted with deuterium, a phenyl group that is substituted or unsubstituted with deuterium, a biphenyl group that is substituted or unsubstituted with deuterium, or a naphthyl group that is substituted or unsubstituted with deuterium.

[0144] In this specification, R1 to R6 may be the same as or different from each other, and each is independently a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, or a deuterated or unsubstituted naphthyl.

[0145] In this specification, R1 to R6 are the same as or different from each other, and each is independently a phenyl substituted with or unsubstituted with deuterium.

[0146] In this specification, R7 to R9 may be the same as or different from each other, and each is independently an alkyl group substituted with or unsubstituted with deuterium, or an aryl group substituted with or unsubstituted with deuterium.

[0147] In this specification, R7 to R9 may be the same as or different from each other, and each is independently an alkyl group with 1 to 10 carbon atoms that is substituted with deuterium or unsubstituted, or an aryl group with 6 to 30 carbon atoms that is substituted with deuterium or unsubstituted.

[0148] In this specification, R7 to R9 may be the same as or different from each other, and each is independently an alkyl group having 1 to 7 carbon atoms that is substituted with deuterium or not substituted, or an aryl group having 6 to 20 carbon atoms that is substituted with deuterium or not substituted.

[0149] In this specification, R7 to R9 may be the same as or different from each other, and each is independently an alkyl group having 1 to 5 carbon atoms that is substituted with deuterium or not substituted, or an aryl group having 6 to 15 carbon atoms that is substituted with deuterium or not substituted.

[0150] In this specification, R7 to R9 may be the same as or different from each other, and each independently represents a methyl group that is substituted or unsubstituted with deuterium, an ethyl group that is substituted or unsubstituted with deuterium, a phenyl group that is substituted or unsubstituted with deuterium, a biphenyl group that is substituted or unsubstituted with deuterium, or a naphthyl group that is substituted or unsubstituted with deuterium.

[0151] In this specification, R7 to R9 may be the same as or different from each other, and each is independently a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, or a deuterated or unsubstituted naphthyl.

[0152] In this specification, R7 to R9 are the same as or different from each other, and each is independently a phenyl substituted with or unsubstituted with deuterium.

[0153] In this specification, R1 to R3 and L1 are bonded to each other with adjacent substituents to form a ring.

[0154] In this specification, R1 and R2 are combined with each other to form a ring.

[0155] In this specification, R2 and R3 are combined with each other to form a ring.

[0156] In this specification, R3 and L1 are combined with each other to form a ring.

[0157] In this specification, R1 and L1 are combined with each other to form a ring.

[0158] In this specification, R1 to R3 are the same or different from each other, each being a deuterated or unsubstituted phenyl group, L1 is a deuterated or unsubstituted phenylene, and R1 and R2 are combined with each other to form a ring.

[0159] In this specification, R1 to R3 are the same or different from each other, each being a deuterated or unsubstituted phenyl group, L1 is a deuterated or unsubstituted phenylene, and R2 and R3 are combined with each other to form a ring.

[0160] In this specification, R1 to R3 may be the same as or different from each other, each being a deuterated or unsubstituted phenyl group, L1 is a deuterated or unsubstituted phenylene group, and R3 and L1 are combined with each other to form a ring.

[0161] In this specification, R1 to R3 may be the same as or different from each other, each being a deuterated or unsubstituted phenyl group, and L1 is a deuterated or unsubstituted phenylene group. R1 and L1 are combined with each other to form a ring.

[0162] In this specification, R4 to R6 and L2 are bonded to each other with adjacent substituents to form a ring.

[0163] In this specification, R4 and R5 are combined with each other to form a ring.

[0164] In this specification, R5 and R6 are combined with each other to form a ring.

[0165] In this specification, R6 and L2 are combined with each other to form a ring.

[0166] In this specification, R4 and L2 are combined with each other to form a ring.

[0167] In this specification, R4 to R6 are the same or different from each other, each being a deuterated or unsubstituted phenyl group, L2 is a deuterated or unsubstituted phenylene, and R4 and R5 are combined with each other to form a ring.

[0168] In this specification, R4 to R6 are the same or different from each other, each being a deuterated or unsubstituted phenyl group, L2 is a deuterated or unsubstituted phenylene, and R5 and R6 are combined with each other to form a ring.

[0169] In this specification, R4 to R6 are the same or different from each other, each being a deuterated or unsubstituted phenyl group, and L2 is a deuterated or unsubstituted phenylene group. R6 and L2 are combined with each other to form a ring.

[0170] In this specification, R4 to R6 are the same or different from each other, each being a deuterated or unsubstituted phenyl group, and L2 is a deuterated or unsubstituted phenylene group. R4 and L2 are combined with each other to form a ring.

[0171] In this specification, R7 to R9 and L are bonded to each other with adjacent substituents to form a ring.

[0172] In this specification, R7 and R8 are combined with each other to form a ring.

[0173] In this specification, R8 and R9 are combined with each other to form a ring.

[0174] In this specification, R9 and L3 are combined with each other to form a ring.

[0175] In this specification, R7 and L3 are combined with each other to form a ring.

[0176] In this specification, R7 to R9 are the same or different from each other, and are phenyl groups that are substituted with deuterium or not substituted. L3 is a phenylene group that is substituted with deuterium or not substituted. R7 and R8 are combined with each other to form a ring.

[0177] In this specification, R7 to R9 are the same or different from each other, and are phenyl groups that are substituted with deuterium or not substituted. L3 is a phenylene group that is substituted with deuterium or not substituted. R8 and R9 are combined with each other to form a ring.

[0178] In this specification, R4 to R6 are the same or different from each other, and are phenyl groups that are substituted with deuterium or not substituted, L2 is a phenylene group that is substituted with deuterium or not substituted, and R9 and L3 are combined with each other to form a ring.

[0179] In this specification, R4 to R6 are the same or different from each other, and are phenyl groups that are substituted with deuterium or not substituted, L2 is a phenylene group that is substituted with deuterium or not substituted, and R7 and L3 are bonded together to form a ring.

[0180] In this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group.

[0181] In this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 30 carbon atoms.

[0182] In this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 20 carbon atoms.

[0183] In this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 15 carbon atoms.

[0184] In this specification, L1 and L2 may be the same as or different from each other, and each is independently an arylene group with 6 to 30 substituted or unsubstituted carbon atoms.

[0185] In this specification, L1 and L2 may be the same as or different from each other, and each is independently an arylene group with 6 to 20 substituted or unsubstituted carbon atoms.

[0186] In this specification, L1 and L2 may be the same as or different from each other, and each is independently an arylene group with 6 to 15 substituted or unsubstituted carbon atoms.

[0187] In this specification, L1 and L2 may be the same as or different from each other, and each is independently an arylene group with 6 to 30 carbon atoms, either substituted with deuterium or unsubstituted.

[0188] In this specification, L1 and L2 may be the same as or different from each other, and each is independently an arylene group with 6 to 20 carbon atoms, either substituted with deuterium or unsubstituted.

[0189] In this specification, L1 and L2 may be the same as or different from each other, and each is independently an aryl group with 6 to 15 carbon atoms, either substituted with deuterium or unsubstituted.

[0190] In this specification, L1 and L2 may be the same as or different from each other, and each is independently a deuterated or unsubstituted phenyl, or a deuterated or unsubstituted divalent naphthyl.

[0191] In this specification, L1 and L2 are the same as or different from each other, and each is independently a phenyl substituted with or unsubstituted with deuterium.

[0192] In this specification, R21 to R24 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0193] In this specification, R21 to R24 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms.

[0194] In this specification, R21 to R24 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl with 3 to 20 carbon atoms.

[0195] In this specification, R21 to R24 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, aryl with 6 to 30 substituted or unsubstituted carbon atoms, or heteroaryl with 3 to 30 substituted or unsubstituted carbon atoms.

[0196] In this specification, R21 to R24 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0197] In this specification, R21 to R24 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, an aryl group with 6 to 30 carbon atoms substituted or unsubstituted with deuterium, or a heteroaryl group with 3 to 30 carbon atoms substituted or unsubstituted with deuterium.

[0198] In this specification, R21 to R24 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, an aryl group with 6 to 20 carbon atoms substituted or unsubstituted with deuterium, or a heteroaryl group with 3 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0199] In this specification, R21 to R24 may be the same as or different from each other, and each independently represents hydrogen, deuterium, a deuterated or unsubstituted phenyl group, a deuterated or unsubstituted naphthyl group, a deuterated or unsubstituted biphenyl group, a deuterated or unsubstituted carbazolyl group, a deuterated or unsubstituted dibenzothiophene group, or a deuterated or unsubstituted dibenzofuranyl group.

[0200] In this specification, R21 to R24 may be the same as or different from each other, and each independently is hydrogen, deuterium, a deuterated or unsubstituted phenyl group, a deuterated or unsubstituted carbazolyl group, or a deuterated or unsubstituted dibenzofuranyl group.

[0201] In this specification, R25 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0202] In this specification, R25 is an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 30 substituted or unsubstituted carbon atoms.

[0203] In this specification, R25 is an aryl group with 6 to 25 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 25 substituted or unsubstituted carbon atoms.

[0204] In this specification, R25 is an aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 20 substituted or unsubstituted carbon atoms.

[0205] In this specification, R25 is an aryl group with 6 to 15 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 15 substituted or unsubstituted carbon atoms.

[0206] In this specification, R25 refers to an aryl group that is substituted or unsubstituted with a heteroaryl group, or a heteroaryl group.

[0207] In this specification, R25 is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with a heteroaryl group having 3 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0208] In this specification, R25 is an aryl group with 6 to 20 carbon atoms that is substituted or unsubstituted with a heteroaryl group having 3 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0209] In this specification, R25 is an aryl group with 6 to 15 carbon atoms that is substituted or unsubstituted with a heteroaryl group having 3 to 15 carbon atoms, or a heteroaryl group having 3 to 15 carbon atoms.

[0210] In this specification, R25 refers to a phenyl group substituted or unsubstituted with a heteroaryl group, a biphenyl group substituted or unsubstituted with a heteroaryl group, a terphenyl group substituted or unsubstituted with a heteroaryl group, an anthraquinone group substituted or unsubstituted with a heteroaryl group, a phenanthrene group substituted or unsubstituted with a heteroaryl group, a naphthyl group substituted or unsubstituted with a heteroaryl group, a carbazole group, a dibenzofuranyl group, a dibenzothiophene group, or a benzo[a]benzyl group. Azolyl, benzofuranyl, benzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl.

[0211] In this specification, R25 is a phenyl, biphenyl, terphenyl, or dibenzofuranyl group that is substituted with or unsubstituted with a carbazoyl group.

[0212] In this specification, R26 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0213] In this specification, R26 is an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 30 substituted or unsubstituted carbon atoms.

[0214] In this specification, R26 is an aryl group with 6 to 25 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 25 substituted or unsubstituted carbon atoms.

[0215] In this specification, R26 is an aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 20 substituted or unsubstituted carbon atoms.

[0216] In this specification, R26 is an aryl group with 6 to 15 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 15 substituted or unsubstituted carbon atoms.

[0217] In this specification, R26 is an aryl group that is substituted or unsubstituted with a heteroaryl group, or a heteroaryl group.

[0218] In this specification, R26 is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with a heteroaryl group having 3 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0219] In this specification, R26 is an aryl group with 6 to 20 carbon atoms that is substituted or unsubstituted with a heteroaryl group having 3 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0220] In this specification, R26 is an aryl group with 6 to 15 carbon atoms that is substituted or unsubstituted with a heteroaryl group having 3 to 15 carbon atoms, or a heteroaryl group having 3 to 15 carbon atoms.

[0221] In this specification, R26 refers to a phenyl group substituted or unsubstituted with a heteroaryl group, a biphenyl group substituted or unsubstituted with a heteroaryl group, a terphenyl group substituted or unsubstituted with a heteroaryl group, an anthraquinone group substituted or unsubstituted with a heteroaryl group, a phenanthrene group substituted or unsubstituted with a heteroaryl group, a naphthyl group substituted or unsubstituted with a heteroaryl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophene group, or a benzo[a]benzyl group. Azolyl, benzofuranyl, benzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl.

[0222] In this specification, R26 is a phenyl, biphenyl, terphenyl, or dibenzofuranyl group that is substituted with or unsubstituted with a carbazoyl group.

[0223] In this specification, L3 refers to a directly bonded, substituted, or unsubstituted aryl group with 6 to 30 carbon atoms.

[0224] In this specification, L3 refers to a directly bonded, substituted, or unsubstituted aryl group with 6 to 20 carbon atoms.

[0225] In this specification, L3 refers to a directly bonded or arylene group having 6 to 30 carbon atoms.

[0226] In this specification, L3 refers to a directly bonded or arylene group having 6 to 20 carbon atoms.

[0227] In this specification, L3 refers to direct bonding or phenylene oxide.

[0228] In this specification, X1 to X3 are N.

[0229] In this specification, X1 is N, and X2 and X3 are CR.

[0230] In this specification, X3 is N, and X1 and X2 are CR.

[0231] In this specification, X2 is N, and X1 and X3 are CR.

[0232] In this specification, X1 and X2 are N, and X3 is CR.

[0233] In this specification, X1 and X3 are N, and X2 is CR.

[0234] In this specification, X2 and X3 are N, and X1 is CR.

[0235] In this specification, HET refers to a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted heteroaryl group.

[0236] In this specification, HET refers to a heteroaryl group that is substituted or unsubstituted with an aryl group, or a heteroaryl group that is substituted or unsubstituted with an aryl group.

[0237] In this specification, HET refers to an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with a heteroaryl group with 3 to 30 carbon atoms, or a heteroaryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with a aryl group with 6 to 30 carbon atoms.

[0238] In this specification, HET is a phenyl group substituted or unsubstituted with an aryl carbazolyl group, a dibenzofuranyl group, a dibenzothiophene group, or a carbazolyl group substituted or unsubstituted with an aryl group.

[0239] In this specification, HET refers to a phenyl group substituted with or unsubstituted with a carbazolyl group, a dibenzofuranyl group, a dibenzothiophene group, or a carbazolyl group substituted with or unsubstituted with a phenyl group.

[0240] In this specification, R11 and R12 are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0241] In this specification, R11 and R12 are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 7 carbon atoms.

[0242] In this specification, R11 and R12 are the same as or different from each other, and each is independently methyl or ethyl.

[0243] In this specification, R13 to R16 may be the same as or different from each other, and each is independently a nitrile group, a halogen group, or an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with an alkyl group, or a ring formed by combining with an adjacent substituent.

[0244] In this specification, R13 to R16 may be the same as or different from each other, and each is independently a nitrile group, a halogen group, or an aryl group with 6 to 20 carbon atoms that is substituted or unsubstituted with an alkyl group, or a ring formed by combining with an adjacent substituent.

[0245] In this specification, R13 to R16 may be the same as or different from each other, and each is independently a nitrile group, a halogen group, or an aryl group that is substituted with or unsubstituted with an alkyl group, or a ring formed by combining with an adjacent substituent.

[0246] In this specification, R13 to R16 may be the same as or different from each other, each being independently a nitrile group, a halogen group, or a phenyl group substituted with or unsubstituted with an alkyl group, or a ring formed by combination with an adjacent substituent.

[0247] In this specification, R13 to R16 may be the same as or different from each other, each being independently a nitrile group, a fluorine group, or a phenyl group substituted with or unsubstituted with a methyl group, or a ring formed by combining with an adjacent substituent.

[0248] In this specification, M refers to a transition metal.

[0249] In this specification, M refers to a Group 6 metal.

[0250] In this specification, M refers to Ir or Pt.

[0251] In this specification, M refers to Pt.

[0252] In this specification, Z1 is a pentagonal or hexacyclic heterocycle containing N.

[0253] In this specification, Z1 refers to a pyridine ring, a pyrazole ring, a pyrrole ring, or an imidazole ring.

[0254] In this specification, the above chemical formula 5 is any one of the following chemical formulas 5-1 to 5-4.

[0255] [Chemical Formula 5-1]

[0256]

[0257] [Chemical Formula 5-2]

[0258]

[0259] [Chemical Formula 5-3]

[0260]

[0261] [Chemical Formula 5-4]

[0262]

[0263] In the above chemical formulas 5-1 to 5-4, R17 to R20, R35, a5, and f to h are defined in the same way as in chemical formula 5.

[0264] R17 is hydrogen, deuterium, nitrile, halogen, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0265] e is an integer from 1 to 3.

[0266] e' is 1 or 2

[0267] e" is an integer from 1 to 4.

[0268] e3 is an integer from 1 to 4.

[0269] When e, e', e" and e3 are 2 or more, the substituents in the parentheses are the same or different from each other.

[0270] In this specification, the first dopant compound represented by the above chemical formula 4 or 5 is a phosphorescent dopant compound.

[0271] In this specification, the second dopant compound represented by the above chemical formula 6 is a fluorescent dopant compound.

[0272] According to one embodiment of this specification, the compound represented by the above chemical formula 1 is any one of the following compounds.

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283] According to one embodiment of this specification, the compound represented by the above chemical formula 2 is any one of the following compounds.

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324] According to one embodiment of this specification, the compound represented by the above chemical formula 3 is any one of the following compounds.

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334] According to one embodiment of this specification, the compound represented by the above chemical formula 4 is any one of the following compounds.

[0335]

[0336]

[0337] According to one embodiment of this specification, the compound represented by the above chemical formula 5 is any one of the following compounds.

[0338]

[0339]

[0340]

[0341]

[0342] According to one embodiment of this specification, the compound represented by the above chemical formula 6 is any one of the following compounds.

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351] The substituents of the compound of the above chemical formula 1 can be combined by methods known in the art, and the type, position or number of substituents can be changed according to techniques known in the art.

[0352] Furthermore, by introducing various substituents into the core structure shown above, compounds possessing the inherent properties of the introduced substituents can be synthesized. For example, by introducing substituents primarily 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 aforementioned core structure, substances satisfying the requirements of each organic layer can be synthesized.

[0353] Furthermore, the organic light-emitting device according to the present invention is characterized in that it includes: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contain the compounds mentioned above.

[0354] The organic light-emitting device of the present invention utilizes the above-mentioned compound to form one or more organic layers. Otherwise, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0355] The aforementioned compounds can be used to form organic layers not only through vacuum evaporation but also through solution coating in the fabrication of organic light-emitting devices. Here, solution coating refers to methods such as spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating, but is not limited to these.

[0356] The organic layers of the organic light-emitting device of the present invention can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of the present invention can have a structure comprising 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, and an electron injection layer as organic layers. However, the structure of the organic light-emitting device is not limited to this, and may include fewer or more organic layers.

[0357] In the organic light-emitting device of the present invention, the organic layer may include one or more of an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron injection and electron transport, and one or more of the aforementioned layers may contain a compound represented by the aforementioned chemical formula 1.

[0358] In another organic light-emitting device, the organic layer may include an electron transport layer or an electron injection layer, which may contain a compound represented by the above chemical formula 1.

[0359] In the organic light-emitting device of the present invention, the organic layer may include one or more of a hole injection layer, a hole transport layer, and a layer that performs both hole injection and hole transport simultaneously, wherein one or more of the aforementioned layers may contain a compound represented by the aforementioned chemical formula 1.

[0360] In another organic light-emitting device, the organic layer may include a hole injection layer or a hole transport layer, which may contain a compound represented by the above chemical formula 1.

[0361] In one embodiment of this specification, the first electrode is the anode and the second electrode is the cathode.

[0362] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0363] (1) Anode / hole transport layer / light-emitting layer / cathode

[0364] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0365] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0366] (4) Anode / Hole transport layer / Light emission layer / Electron transport layer / Cathode

[0367] (5) Anode / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0368] (6) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0369] (7) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0370] (8) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0371] (9) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0372] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0373] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0374] (12) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0375] (13) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0376] (14) Anode / Hole transport layer / Light emission layer / Hole suppression layer / Electron transport layer / Cathode

[0377] (15) Anode / Hole transport layer / Light emission layer / Hole suppression layer / Electron transport layer / Electron injection layer / Cathode

[0378] (16) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole suppression layer / Electron transport layer / Cathode

[0379] (17) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Suppression Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0380] (18) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Hole Blocking Layer / Electron Injection and Transport Layer / Cathode

[0381] The organic light-emitting device of the present invention can have the following structure: Figure 1 The structure shown is not limited to this.

[0382] Figure 1 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.

[0383] Figure 2 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 4 are sequentially stacked on a substrate 1.

[0384] For example, the organic light-emitting device according to the present invention can be manufactured as follows: An anode is formed by depositing a metal or a conductive metal oxide or alloy thereof onto a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation. Then, an organic layer comprising one or more layers selected from a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron transport and electron injection is formed on the anode. Finally, a material suitable for use as a cathode is deposited onto the organic layer. Alternatively, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto a substrate.

[0385] The aforementioned organic layer can be a multilayer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, but is not limited to this; it can also be a single-layer structure. Furthermore, the aforementioned organic layer can be manufactured in smaller quantities using various polymer materials and solvent processes other than vapor deposition, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0386] The anode described above is the electrode for injecting holes. As the anode material, it is generally preferred to be a material with a high work function in order to enable holes to be smoothly injected into the organic layer. Specific examples of anode materials that can be used in this 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), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0387] The cathode described above is the electrode into which electrons are injected. As a cathode material, it is generally preferred to be a material with a low work function in order to facilitate the injection of electrons into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0388] The aforementioned hole injection layer facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is one that can effectively receive holes from the anode at low voltages. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene. The thickness of the hole injection layer can range from 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, it has the advantage of preventing a decrease in hole injection characteristics; when it is less than 150 nm, it has the advantage of preventing an increase in driving voltage to improve hole migration when the hole injection layer is too thick.

[0389] According to one embodiment of this specification, the hole injection layer comprises, but is not limited to, a compound represented by the chemical formula HI-2.

[0390] [Chemical formula HI-2]

[0391]

[0392] In the above chemical formula HI-2,

[0393] X'1 to X'3 may be the same as or different from each other, and each is independently a hydrogen, deuterium, or halogen group.

[0394] R309 to R314 may be the same as or different from each other, and each is independently hydrogen, deuterium, nitrile, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0395] x1' to x3' are each an integer from 1 to 4. When they are 2 or more, the substituents in the parentheses are the same or different from each other.

[0396] According to one embodiment of this specification, X'1 to X'3 are halogen groups.

[0397] According to one embodiment of this specification, X'1 to X'3 are F or Cl.

[0398] According to one embodiment of this specification, X'1 to X'3 are F.

[0399] According to one embodiment of this specification, R309 to R314 may be the same as or different from each other, and each is independently hydrogen, deuterium, nitrile, substituted or unsubstituted alkyl, or substituted or unsubstituted amine.

[0400] According to one embodiment of this specification, R309 to R314 may be the same as or different from each other, and each is independently hydrogen, deuterium or nitrile group.

[0401] According to one embodiment of this specification, R309 to R314 are nitrile groups.

[0402] According to one embodiment of this specification, the above-mentioned chemical formula HI-2 is represented by the following compound.

[0403]

[0404] In this specification, the hole injection layer may contain other substances besides the substance with the chemical formula HI-2.

[0405] In this specification, the hole injection layer described above comprises a compound with the chemical formula HI-2.

[0406] [Chemical formula HI-2]

[0407]

[0408] In the above chemical formula HI-2,

[0409] R400 to R402 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amino, substituted or unsubstituted heteroaryl, and combinations thereof, or may be combined with adjacent groups to form substituted or unsubstituted rings.

[0410] L402 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0411] According to one embodiment of this specification, L402 is a phenylene oxide.

[0412] According to one embodiment of this specification, R400 to R402 may be the same as or different from each other, and each independently is selected from any one of substituted or unsubstituted aryl, substituted or unsubstituted amino, substituted or unsubstituted heteroaryl, and combinations thereof.

[0413] According to one embodiment of this specification, R402 is selected from carbazole groups that are substituted with or unsubstituted with phenyl groups, and combinations thereof.

[0414] According to one embodiment of this specification, R400 and R401 may be the same as or different from each other, each being independently a substituted or unsubstituted aryl group, or combined with adjacent groups to form an alkyl-substituted aromatic hydrocarbon ring.

[0415] According to one embodiment of this specification, R400 and R401 may be the same as or different from each other, and each is independently an aryl group that is substituted with or unsubstituted with an alkyl group.

[0416] According to one embodiment of this specification, R400 and R401 may be the same as or different from each other, and each is independently phenyl, biphenyl or dimethylfluorenyl.

[0417] According to one embodiment of this specification, the above chemical formula HI-2 is selected from the following compounds.

[0418]

[0419] The aforementioned hole transport layer facilitates hole transport. The hole transport material is capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; materials with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but these are not limited to these.

[0420] According to one embodiment of this specification, the hole transport layer comprises, but is not limited to, a compound represented by the chemical formula HT-1.

[0421] [Chemical formula HT-1]

[0422]

[0423] In the above chemical formula HT-1,

[0424] L311 to L313 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

[0425] R311 to R313 may be the same as or different from each other, and each independently is selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or is combined with adjacent groups to form substituted or unsubstituted rings.

[0426] According to one embodiment of this specification, R311 to R313 may be the same as or different from each other, and each independently is selected from any one of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, and combinations thereof.

[0427] According to one embodiment of this specification, R311 to R313 may be the same as or different from each other, and each independently is selected from any one of substituted or unsubstituted carbazolyl, substituted or unsubstituted phenyl, biphenyl, and combinations thereof.

[0428] According to one embodiment of this specification, R311 to R313 may be the same as or different from each other, and each is independently a carbazole group, dimethylfluorenyl group, or biphenyl group substituted with phenyl.

[0429] According to one embodiment of this specification, L311 to L313 may be the same as or different from each other, and each is independently directly bonded, arylene or heteroarylene.

[0430] According to one embodiment of this specification, L311 to L313 may be the same as or different from each other, and each is independently directly bonded or phenylene.

[0431] According to one embodiment of this specification, the above-mentioned chemical formula HT-1 is represented by the following compound.

[0432]

[0433] A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, which may contain materials known in the art for hole injection or transport.

[0434] An electron blocking layer may be disposed between the hole transport layer and the light-emitting layer. This electron blocking layer may use the aforementioned spirocyclic compound or materials known in this art.

[0435] The aforementioned luminescent layer can emit red, green, or blue light and can be formed from phosphorescent or fluorescent substances. The luminescent substance is capable of receiving holes and electrons from the hole transport layer and electron transport layer respectively, and combining them to emit light in the visible light region; preferably, it is a substance with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds of the azole, benzothiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV) polymers; spirocyclic compounds; polyfluorene, fluorene, etc., but not limited to these.

[0436] The main materials for the luminescent layer include aromatic fused-ring derivatives or heterocyclic compounds. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited to these.

[0437] When the luminescent layer emits red light, phosphorescent dopants such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum) can be used; or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the luminescent layer emits green light, phosphorescent materials such as Ir(ppy)3 (facilitated tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used as luminescent dopants, but these are not limited to these. When the luminescent layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used as luminescent dopants; or fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene arylene (DSA), PFO-based polymers, PPV-based polymers, etc., but these are not limited to these.

[0438] A hole suppression layer can be provided between the electron transport layer and the light-emitting layer, and materials known in this art can be used.

[0439] The aforementioned electron transport layer facilitates electron transport. The electron transport material is one that can effectively receive electrons from the cathode and transfer them to the light-emitting layer; materials with high electron mobility are suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, and hydroxyflavonoid-metal complexes, but these are not limited to these. The thickness of the electron transport layer can range from 1 to 50 nm. When the thickness of the electron transport layer is greater than 1 nm, it has the advantage of preventing a decrease in electron transport properties; when it is less than 50 nm, it has the advantage of preventing an increase in driving voltage to improve electron migration when the electron transport layer is too thick.

[0440] The aforementioned electron injection layer facilitates electron injection. Preferred electron injection materials include compounds that possess electron transport capabilities, effectively inject electrons from the cathode, exhibit excellent electron injection performance for the light-emitting layer or material, prevent excitons generated in the light-emitting layer from migrating to the hole injection layer, and demonstrate excellent thin-film formation ability. Specifically, these include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0441] According to one embodiment of this specification, the electron injection and transport layer comprises a compound with the following chemical formula EI-1.

[0442] [Chemical Formula EI-1]

[0443]

[0444] In the above chemical formula EI-1,

[0445] At least one of Z11 to Z13 is N, and the rest are CH.

[0446] At least one of Z14 to Z16 is N, and the rest are CH.

[0447] L701 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0448] Ar701 to Ar704 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0449] l701 is an integer from 1 to 4. When l701 is a complex number, l701 can be the same or different from each other.

[0450] According to one embodiment of this specification, the L701 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0451] According to one embodiment of this specification, L701 is phenylene, biphenylene, or naphthylene.

[0452] According to one embodiment of this specification, L701 is phenylene or naphthylene.

[0453] According to one embodiment of this specification, Ar701 to Ar704 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms, either substituted or unsubstituted.

[0454] According to one embodiment of this specification, Ar701 to Ar704 are phenyl groups.

[0455] According to one embodiment of this specification, the above-mentioned chemical formula HB-1 is represented by the following compound.

[0456]

[0457] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, 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, but are not limited to these.

[0458] The aforementioned hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed using the same conditions as the electron injection layer. Specifically, there are... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0459] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0460] The organic light-emitting device of the present invention utilizes the above-mentioned compound to form one or more organic layers. Otherwise, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0461] The method for manufacturing the compound of chemical formula 1 and the method for manufacturing organic light-emitting devices using the compound are specifically described in the following examples. However, the following examples are for illustrative purposes only and the scope of the invention is not limited thereto.

[0462] Methods of implementing the invention

[0463] In the following reaction formulas, the types and numbers of substituents can be appropriately selected from known starting materials by those skilled in the art to synthesize various types of intermediates. The types and conditions of the reactions can utilize techniques known in this art.

[0464] Conventional synthetic methods for chemical formulas 1 and 2

[0465]

[0466] In the above synthesis method, R1 to R6, R21 to R25, a1 to a4, L1 and L2 are the same as those defined in the above chemical formulas 1 and 2.

[0467] Conventional synthetic methods for chemical formula 3

[0468]

[0469] In the above synthesis method, R7 to R9, R26, X1 to X3, HET and a6 are defined as in the above chemical formula 3.

[0470] Conventional synthetic methods for chemical formulas 4 and 5

[0471]

[0472] In the above synthetic method, R17 to R20, R35, e to h and a5 are the same as defined in chemical formulas 4 and 5 above.

[0473] Conventional Synthesis Methods of Chemical Formula 6

[0474]

[0475] In the above synthesis method, A1 to A3, B1 and B2 are defined in the same way as in the above chemical formula 6.

[0476] If the manufacturing formulas described in the examples of this specification and the intermediates described above are appropriately combined based on common technical knowledge, all the compounds of chemical formula 1 described in this specification can be manufactured.

[0477] Synthesis Example 1. Synthesis of Compound H1-1

[0478]

[0479] Under a nitrogen atmosphere, 5.0 g of (2-bromophenyl)triphenylsilane, 4.0 g of 9H-2,9'-bicarbazole, and 1.7 g of sodium tert-butoxide (NaOtBu) were added to 100 mL of toluene, and the mixture was stirred and refluxed. Then, 0.12 g of bis(tri-tert-butylphosphine)palladium(0) (Pd(PtBu3)2) was added, and the mixture was heated and stirred for 10 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and water and NH4Cl solution (aq.) were added. The organic layer was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was distilled under reduced pressure and purified by recrystallization (toluene / ethyl acetate) to obtain 5.2 g of compound H1-1. (Yield 65%, Mass): [M] + ]=667)

[0480] Synthesis Example 2. Synthesis of Compound H1-2

[0481]

[0482] Compound H1-2 was prepared by means of the same method as that used for preparing compound H1-1 in Synthetic Example 1, except that 5.0 g of (3-bromophenyl-2,4,5,6-d4)tris(phenyl-d5)silane was used instead of the starting material (2-bromophenyl)triphenylsilane, and 4.0 g of 9H-3,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d15 was used instead of 9H-2,9'-bicarbazole. Thus, 6.6 g of compound H1-2 was obtained. (Yield 82%, quality [M]) + ]=702)

[0483] Synthesis Example 3. Synthesis of Compound H1-3

[0484]

[0485] Compound H1-3 was prepared by means of the same method as that used for compound H1-1 in Synthetic Example 1, except that 5.0 g of (4-bromophenyl-2,3,5,6-d4)tris(phenyl-d5)silane was used instead of the starting material (2-bromophenyl)triphenylsilane, and 4.0 g of 9H-4,9'-bicarbazole-1,1',2,2',3,3',4',5,5',6,6',7,7',8,8'-d15 was used instead of 9H-2,9'-bicarbazole. Thus, 5.5 g of compound H1-3 was obtained. (Yield 68%, quality [M]) + ]=702)

[0486] Synthesis Example 4. Synthesis of Compound H1-4

[0487] 1) Synthesis of intermediate 1-1

[0488]

[0489] Under a nitrogen atmosphere, add 5.0 g of 3'-bromo-9H-3,9'-bicarbazole, 2.8 g of dibenzo[b,d]furan-4-ylboronicacid, 3.4 g of potassium carbonate, and 80 mL of dioxin. After adding alkane and 20 mL of water, 0.28 g of tetrakis(triphenylhosphine)palladium(0)[Pd(PPh3)4] was added, and the mixture was heated at 130 °C for 3 hours with stirring. After the reaction was complete, the reaction solution was cooled to room temperature, water and toluene were added, and the mixture was separated. The solution was then treated with anhydrous MgSO4 and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 4.9 g of intermediate 1-1. (Yield 81%, mass [M]) + ]=499)

[0490] 2) Synthesis of compound H1-4

[0491]

[0492] Compound H1-4 was prepared by replacing the starting material (2-bromophenyl)triphenylsilane with 4.0 g of (3-bromophenyl)triphenylsilane and 9H-2,9'-bicarbazole with 4.9 g of intermediate 1-1, otherwise by the same method as that used to prepare compound H1-1 in Synthetic Example 1, thereby obtaining 4.2 g of compound H1-4. (Yield 76%, mass [M]) + ]=834)

[0493] Synthesis Example 5. Synthesis of Compound H1-5

[0494]

[0495] Compound H1-5 was prepared by replacing the starting material (2-bromophenyl)triphenylsilane with 5.0 g of (3-bromophenyl)triphenylsilane and replacing 9H-2,9'-bicarbazole with 6.0 g of 9H-3,9':4',9"-tercarbazole, otherwise by the same method as that used to prepare compound H1-1 in Synthetic Example 1, thereby obtaining 7.8 g of compound H1-5. (Yield 78%, mass [M]) + ]=833)

[0496] Synthesis Example 6. Synthesis of Compound H1-6

[0497]

[0498] Compound H1-6 was prepared by means of the same method as that used in Synthetic Example 1, by replacing 5.0 g of 1-chloro-5,5-diphenyl-5H-dibenzo[b,d]silole with 4.8 g of 9H-3,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d15 with 9H-2,9'-bicarbazole. Thus, 6.8 g of compound H1-6 was obtained. (Yield 74%, mass [M]) + ]=680)

[0499] Synthesis Example 7. Synthesis of Compound H2-1

[0500] 1) Synthesis of intermediate 2-1

[0501]

[0502] Under a nitrogen atmosphere, add 5.0 g of 3-bromo-9H-carbazole, 10.3 g of triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 5.6 g of potassium carbonate, and 160 mL of dioxaborolan. After adding 40 mL of alkyl and water, 0.5 g of tetra(triphenylphosphine)palladium(0)(Pd(PPh3)4) was added, and the mixture was heated at 130 °C for 6 hours with stirring. After the reaction was complete, the reaction solution was cooled to room temperature, water and toluene were added, and the mixture was separated. The solution was then treated with anhydrous MgSO4 and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 8.1 g of intermediate 2-1. (Yield 79%, mass [M]) + ]=502)

[0503] 2) Synthesis of compound H2-1

[0504]

[0505] Under a nitrogen atmosphere, 3.3 g of 3-bromo-9-(dibenzo[b,d]furan-1-yl)-9H-carbazole, 4.0 g of intermediate 2-1, and 1.1 g of sodium tert-butoxide (NaOtBu) were added to 70 mL of toluene, and the mixture was stirred and refluxed. Then, 0.1 g of bis(tritert-butylphosphine)palladium(O)(Pd(PtBu3)2) was added, and the mixture was heated and stirred for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and water and NH4Cl solution were added. The organic layer was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / ethyl acetate) to obtain 4.6 g of compound H2-1. (Yield 70%, mass: [M]) + ]=834)

[0506] Synthesis Example 8. Synthesis of Compound H2-2

[0507]

[0508] Using 3.1 g of 9-([1,1'-biphenyl]-3-yl)-3-bromo-9H-carbazole instead of the starting material 3-bromo-9-(dibenzo[b,d]furan-1-yl)-9H-carbazole, compound H2-2 was prepared by the same method as that used to prepare compound H2-1 in Synthetic Example 7, thereby obtaining 5.2 g of compound H2-2. (Yield 80%, mass [M] + ]=820)

[0509] Synthesis Example 9. Synthesis of Compound H2-3

[0510] 1) Synthesis of intermediate 2-2

[0511]

[0512] Using 10.3 g of triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane instead of the starting material triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, and using 5.0 g of 3-bromo-9H-carbazole instead of 3-bromo-9H-carbazole, 7.8 g of intermediate 2-2 was obtained by the same method as that used to produce intermediate 2-1 in Synthetic Example 7. (Yield 77%, mass [M]) + ]=502)

[0513] 2) Synthesis of compound H2-3

[0514]

[0515] Intermediate 2-2 was used in place of intermediate 2-1 (3.5 g), and 9-([1,1':3',1”-terphenyl]-2'-yl)-4-chloro-9H-carbazole (9-([1,1':3',1”-terphenyl]-2'-yl)-4-chloro-9H-carbazole) was used in place of the starting material 3-bromo-9-(dibenzo[b,d]furan-1-yl)-9H-carbazole. Otherwise, compound H2-3 was prepared by the same method as that used to prepare compound H2-1 in Synthetic Example 7, thereby obtaining 4.6 g of compound H2-3. (Yield 74%, mass [M] + ]=896)

[0516] Synthesis Example 10. Synthesis of Compound H2-4

[0517]

[0518] Intermediate 2-2 was used in place of intermediate 2-1 (3.5 g), and 9-([1,1'-biphenyl]-2-yl)-4-chloro-9H-carbazole was used in place of the starting material 3-bromo-9-(dibenzo[b,d]furan-1-yl)-9H-carbazole (2.4 g). Otherwise, compound H2-4 was prepared by the same method as that used for compound H2-1 in Synthetic Example 7, thereby obtaining 4.0 g of compound H2-4. (Yield 78%, mass [M] + ]=744)

[0519] Synthesis Example 11. Synthesis of Compound H2-5

[0520] 1) Synthesis of intermediates 2-3

[0521]

[0522] Under a nitrogen atmosphere, 5.0 g of 4-chloro-9H-carbazole, 12.6 g of triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 6.9 g of potassium carbonate, and 200 mL of dioxaborolan were added. After adding 50 mL of alkyl and water, 0.57 g of tetra(triphenylphosphine)palladium(O)(Pd(PPh3)4) was added, and the mixture was heated at 130 °C for 6 hours with stirring. After the reaction was complete, the reaction solution was cooled to room temperature, water and toluene were added, and the mixture was separated. The solution was then treated with anhydrous MgSO4 and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 10 g of intermediate 2-3. (Yield 80%, mass [M]) + ]=502)

[0523] 2) Synthesis of compound H2-5

[0524]

[0525] Intermediate 2-1 was replaced with 10 g of intermediate 2-3, and the starting material 3-bromo-9-phenyl-9H-carbazole was replaced with 6.4 g of 3-bromo-9-phenyl-9H-carbazole. Otherwise, compound H2-5 was prepared by the same method as that used for compound H2-1 in Synthetic Example 7, thereby obtaining 11.1 g of compound H2-5. (Yield 76%, mass [M] + ]=744)

[0526] Synthesis Example 12. Synthesis of Compound H2-6

[0527] 1) Synthesis of intermediates 2-4

[0528]

[0529] Using 10.3 g of 5,5-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-dibenzo[b,d]silole instead of the starting material triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, intermediate 2-4 was prepared by the same method as that used for intermediate 2-1 in Synthetic Example 7, thereby obtaining 6.1 g of intermediate 2-4. (Yield 60%, mass [M] + ] = 500)

[0530] 2) Synthesis of compound H2-6

[0531]

[0532] Intermediate 2-4 was used instead of intermediate 2-1 (6.1 g), and 9-([1,1'-biphenyl]-3-yl)-3-bromo-9H-carbazole was used instead of the starting material 3-bromo-9-(dibenzo[b,d]furan-1-yl)-9H-carbazole. Otherwise, compound H2-6 was prepared by the same method as that used for compound H2-1 in Synthetic Example 7, thereby obtaining 5.5 g of compound H2-6. (Yield 56%, mass [M] + ]=818)

[0533] Synthesis Example 13. Synthesis of Compound H3-1

[0534]

[0535] Under a nitrogen atmosphere, 5.0 g of 9-(4-chloro-6-(3-(tris(phenyl-d5)silyl)phenyl-2,4,5,6-d4)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8(9-(4-chloro-6-(3-(tris(phenyl-d5)silyl)phenyl-2,4,5,6-d4)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8) and 1.9 g of (dibenzo[b,d]furan-3-yl-d7)boronic acid were added. After adding 2.2 g of potassium carbonate, 56 mL of tetrahydrofuran, and 14 mL of water, 0.18 g of tetra(triphenylphosphine)palladium(O)(Pd(PPh3)4) was added, and the mixture was heated at 100 °C for 4 hours with stirring. After the reaction was completed, the reaction solution was cooled to room temperature, water and toluene were added, and the mixture was separated. The solution was then treated with anhydrous MgSO4 and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 5.1 g of compound H3-1. (Yield 84%, mass [M]) + ]=782)

[0536] Synthesis Example 14. Synthesis of Compound H3-2

[0537]

[0538] 5.0 g of 9-(4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole was used instead of the starting material 9-(4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole. 4.0 g of 9-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (9-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole) was used in place of (dibenzo[b,d]furan-3-yl-d7)boronic acid, otherwise it was prepared by the same method as that used to prepare compound H3-1 in Synthetic Example 13, thereby obtaining 5.6 g of compound H3-2. (Yield 77%, mass [M] + ]=899)

[0539] Synthesis Example 15. Synthesis of Compound H3-3

[0540]

[0541] Using 5.0 g of 9-(4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole instead of the starting material 9-(4-chloro-6-(3-(tri(phenyl-d5)silyl)phenyl-2,4,5,6-d4)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8, and using 2.6 g of (2-(9H-carbazol-9-yl)phenyl)boronic acid instead of (dibenzo[b,d]furan-3-yl-d7)boronic acid, 4.9 g of compound H3-3 was obtained by the same method as that used to produce compound H3-1 in Synthetic Example 13. (Yield 73%, mass [M] + ]=823)

[0542] Synthesis Example 16. Synthesis of Compound H3-4

[0543]

[0544] Use 5.0 g of 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8)

[0545] (9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8)) instead of the starting material 9-(4-chloro-6-(3-(tris(phenyl-d5)silyl)phenyl-2,4,5,6-d4)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8), using 5.7 g of tris(phenyl-d5)(3-(4,4,5,5-tetramethyl-1,3)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8). 2-Dioxaborolan-2-yl)phenyl-2,4,5,6-d4)silane (tris(phenyl-d5)(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-2,4,5,6-d4)silane) was substituted for (dibenzo[b,d]furan-3-yl-d7)boronic acid. Otherwise, 6.6 g of compound H3-4 was obtained by the same method as that used to produce compound H3-1 in Synthetic Example 13. (Yield 78%, mass [M] + ]=782)

[0546] Synthesis Example 17. Synthesis of Compound H3-5

[0547]

[0548] 5.0 g of 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) was used instead of the starting material 9-(4-chloro-6-(3-(tris(phenyl-d5)silyl)phenyl-2,4,5,6-d4)-1,3,5-triazine-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 was used, along with 5.7 g of 5,5-diphenyl-2-(4 4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-dibenzo[b,d]silole (5,5-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-dibenzo[b,d]silole) was used instead of (dibenzo[b,d]furan-3-yl-d7)boronic acid. Otherwise, 6.0 g of compound H3-5 was obtained by the same method as that used to produce compound H3-1 in Synthetic Example 13. (Yield 72%, mass [M] + ]=744)

[0549] Synthesis Example 18. Synthesis of Compound D4

[0550] 1) Synthesis of intermediate 4-1

[0551]

[0552] Under a nitrogen atmosphere, add 10 g of 6,6'-(propane-2,2-diyl)bis(2-chloropyridine), 27 g of 4,4,5,5-tetramethyl-2-(2',4',6'-trimethyl-[1,1'-biphenyl]-3-yl)-1,3,2-dioxaborolane, 32 g of potassium phosphate, and 280 mL of dichloropyridine. After adding alkane and 70 mL of water, 1.0 g of tris(dibenzylideneacetone)dipalladium(0) [Tris(dibenzylideneacetone)dipalladium(0)] (Pd2dba3) and 0.9 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl] (SPhos) were added, and the mixture was heated at 130 °C for 18 hours with stirring. After the reaction was completed, the reaction solution was cooled to room temperature, water and toluene were added, and the mixture was separated. The solution was then treated with MgSO4 (anhydrous) and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 16 g of intermediate 4-1. (Yield 55%, mass [M + ]=587)

[0553] 2) Synthesis of compound D4

[0554]

[0555] Under a nitrogen atmosphere, 16 g of intermediate 4-1, 14 g of K3PtCl5, and 100 mL of acetic acid were added, and the mixture was heated and stirred for 2 days. After the reaction was complete, the reaction solution was cooled to room temperature, and water and NaHCO3 solution were added. Ethyl acetate was added, and the mixture was separated. The solution was then treated with anhydrous MgSO4 and filtered. The filtered solution was removed by distillation under reduced pressure and purified by column chromatography (ethyl acetate / hexane) to obtain 2.1 g of compound D4. (Yield 13%, mass [M]) + ]=780)

[0556] Synthesis Example 19. Synthesis of Compound D5-1

[0557] 1) Synthesis of intermediate 5-1

[0558]

[0559] Under a nitrogen atmosphere, 20 g of 1-(3-bromophenyl)-1H-benzo[d]imidazole, 23 g of 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazol-2-ol, 31 g of potassium phosphate, 1.4 g of copper iodide (CuI), 1.8 g of pyridinecarboxylic acid, and 500 mL of dimethyl sulfoxide (DMSO) were added, and the mixture was heated at 150 °C for 72 hours with stirring. After the reaction was completed, the reaction solution was cooled to room temperature, water and ethyl acetate were added, and the mixture was separated. The solution was then treated with anhydrous MgSO4 and filtered. The filtered solution was removed by distillation under reduced pressure and purified by column chromatography (ethyl acetate / hexane) to obtain 30 g of intermediate 5-1. (Yield 81%, quality [M]) + ]=509)

[0560] 1) Synthesis of intermediate 5-2

[0561]

[0562] Under a nitrogen atmosphere, 15 g of intermediate 5-1, 11.2 g of 1,3-di-tert-butyl-5-iodobenzene, and 200 mL of toluene were added, and the mixture was heated at 100 °C for 50 hours with stirring. After the reaction was complete, the reaction solution was cooled to room temperature, and the resulting solid was filtered and washed with diethyl ether. 200 mL of methanol and 20 mL of water were added to the obtained solid, and the mixture was stirred and dissolved. Then, 7.2 g of ammonium hexafluorophosphate (NH4PF6) was added, and the mixture was stirred at room temperature for 3 days. After the reaction was complete, water was added, and the mixture was filtered and washed with diethyl ether. The washed solid was dried to obtain 10 g of intermediate 5-2. (Yield 49%, mass [M]) + ]=698)

[0563] 2) Synthesis of compound D5-1

[0564]

[0565] Under a nitrogen atmosphere, 10 g of intermediate 5-2, 3.5 g of sodium acetate, 5.9 g of dichloro(1,5-cyclooctadiene)platinum (Pt(COD)Cl2), and 100 mL of dimethylformamide (DMF) were added, and the mixture was heated at 120 °C for 72 hours with stirring. After the reaction was completed, the reaction solution was cooled to room temperature, water and ethyl acetate were added, and the mixture was separated. The solution was then treated with anhydrous MgSO4 and filtered. The filtered solution was removed by distillation under reduced pressure and purified by column chromatography (ethyl acetate / hexane) to obtain 1.1 g of compound D5-1. (Yield 9%, mass [M]) + ]=891)

[0566] Synthesis Example 20. Synthesis of Compound D5-2

[0567] 1) Synthesis of intermediate 5-3

[0568]

[0569] Using 15 g of 2'-bromo-1,1':3',1”-terphenyl-2,2”,3,3”,4,4',4”,5,5',5”,6,6',6”-d13 (2'-bromo-1,1':3',1”-terphenyl-2,2”,3,3”,4,4',4”,5,5',5”,6,6',6”-d13) instead of the starting material 1,3-di-tert-butyl-5-iodobenzene, intermediate 5-3 was prepared by the same method as that used for preparing intermediate 5-2 of compound 19, thereby obtaining 10 g of intermediate 5-3. (Yield 45%, mass [M]) + ]=752)

[0570] 2) Synthesis of compound D5-2

[0571]

[0572] Using 10g of intermediate 5-3 instead of starting material intermediate 5-2, and otherwise prepared by the same method as that used to prepare compound D5-1 in Synthetic Example 19, 1.0g of compound D5-2 was obtained. (Yield 8%, mass [M]) + ]=944)

[0573] Synthesis Example 21. Synthesis of Compound D6-1

[0574] 1) Synthesis of intermediate 6-1

[0575]

[0576] Under a nitrogen atmosphere, 23 g of bis(4-(tert-butyl)phenyl)amine, 10 g of 1,3-dibromo-5-methylbenzene, and 12 g of sodium tert-butoxide (NaOtBu) were added to 400 ml of toluene, and the mixture was stirred and refluxed. Then, 0.2 g of bis(tritert-butylphosphine)palladium(O)(Pd(PtBu3)2) was added, and the mixture was heated and stirred for 1 hour. After the reaction was completed, the reaction solution was cooled to room temperature, and water and NH4Cl solution were added. The organic layer was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was distilled under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 20 g of intermediate 6-1. (Yield 77%, mass: [M]) + ]=652)

[0577] 2) Synthesis of compound D6-1

[0578]

[0579] Under a nitrogen atmosphere, 14.4 g of boron triiodide was added to a flask containing 20 g of intermediate 6-1 dissolved in 300 mL of 1,2-dichlorobenzene (DCB), and the mixture was stirred at 150 °C for 3 hours. After the reaction was complete, the reaction solution was cooled to room temperature, and water and sodium thiosulfate solution were added to separate the layers. The solution was then treated with anhydrous MgSO4 and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 6.2 g of compound D6-1. (Yield 31%, mass [M]) + ]=659)

[0580] Synthesis Example 22. Synthesis of Compound D6-2

[0581] 1) Synthesis of intermediate 6-2

[0582]

[0583] Under a nitrogen atmosphere, 11 g of bis(4-(tert-butyl)phenyl)amine, 10 g of 1-bromo-3-(tert-butyl)-5-chlorobenzene, and 12 g of sodium tert-butoxide (NaOtBu) were added to 100 ml of toluene, and the mixture was stirred and refluxed. Then, 0.2 g of bis(tritert-butylphosphine)palladium(O)(Pd(PtBu3)2) was added, and the mixture was heated and stirred for 2 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water and NH4Cl solution were added, the organic layer was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was distilled under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 14 g of intermediate 6-2. (Yield 78%, mass: [M]) + ]=449)

[0584] 2) Synthesis of intermediate 6-3

[0585]

[0586] Under a nitrogen atmosphere, 14 g of intermediate 6-2, 9.3 g of 4-(tert-butyl)aniline, and 4.5 g of sodium tert-butoxide (NaOtBu) were added to 300 ml of toluene, and the mixture was stirred and refluxed. Then, 0.32 g of bis(tritert-butylphosphine)palladium(0)(Pd(PtBu3)2) was added, and the mixture was heated and stirred for 4 hours. After the reaction was complete, 10 g of 3-bromo-5-(tert-butyl)benzo[b]thiophene and 3.0 g of sodium tert-butoxide (NaOtBu) were added, and the mixture was stirred for 3 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water and NH4Cl solution were added, the organic layer was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was removed by distillation under reduced pressure and purified by column chromatography to obtain 18.5 g of intermediate 6-3. (Yield 79%, mass: [M]) + ]=750)

[0587] 3) Synthesis of compound D6-2

[0588]

[0589] Under a nitrogen atmosphere, 11.6 g of boron triiodide was added to a flask containing 18.5 g of intermediate 6-3 dissolved in 250 mL of 1,2-dichlorobenzene (DCB), and the mixture was stirred at 150 °C for 6 hours. After the reaction was complete, the reaction solution was cooled to room temperature, and water and sodium thiosulfate solution were added to separate the layers. The solution was then treated with anhydrous MgSO4 and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 5.6 g of compound D6-2. (Yield 30%, mass [M]) + ]=757)

[0590] Example 1-1

[0591] ITO (Indium Tin Oxide) A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0592] On the ITO transparent electrode, which is thus prepared as the anode, compounds HT1 and HI1 are mixed in a molar ratio of 98:2. A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. A compound represented by the chemical formula HT1 is then deposited onto the hole injection layer. A hole transport layer is formed by vacuum evaporation. Then, on the aforementioned hole transport layer, a film thickness of [missing information] is applied. An electron blocking layer is formed by vacuum evaporation of compound HT1 of chemical formula 1. Next, on the electron blocking layer, a compound consisting of a 1:1 (or 2:1) mixture of compound H1-1 (represented by chemical formula 1) and compound H3-1 (represented by chemical formula 3) serving as the main body of the light-emitting layer, and a compound represented by chemical formula D5-1 serving as a dopant for the light-emitting layer, are vacuum evaporated at a weight ratio of 15%. Another dopant, a compound represented by chemical formula D6-1, serving as another dopant for the light-emitting layer, is also vacuum evaporated at a weight ratio of 1%, thereby forming a light-emitting layer. On the light-emitting layer, a film thickness of... A hole-blocking layer is formed by vacuum evaporation of compound H3-1, represented by chemical formula 3. Next, a compound represented by chemical formula ET1 and a compound represented by chemical formula LiQ are vacuum evaporated onto the hole-blocking layer in a 1:1 weight ratio, thereby achieving… The thickness forms an electron injection and transport layer. On this electron injection and transport layer, lithium fluoride (LiF) is sequentially applied... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness.

[0593]

[0594] During the above process, the evaporation rate of organic matter is maintained. Lithium fluoride maintenance of the cathode The evaporation rate of aluminum maintains The evaporation rate was such that the vacuum level was maintained at 2×10⁻⁶ during evaporation. -7 ~5×10 -6 This led to the creation of organic light-emitting devices.

[0595] Examples 1-2 to Examples 1-14

[0596] Organic light-emitting devices were manufactured using the compounds listed in Table 1 below, except by the same method as in Examples 1-1 above.

[0597] Comparative Examples 1-1 to 1-7

[0598] Organic light-emitting devices were manufactured using the compounds listed in Table 1 below, except for the methods described in Examples 1-1 above. The compounds BD1 to BD3 used in Table 1 below are shown below.

[0599]

[0600] Experimental Example 1

[0601] When current was applied to the organic light-emitting devices manufactured in the above embodiments and comparative examples, the voltage, efficiency, and lifetime were measured, and the results are shown in Table 1 below.

[0602] In Table 1 below, T90 refers to the time required for the brightness to decrease from the initial brightness (1500 nits) to 90%.

[0603] [Table 1]

[0604]

[0605]

[0606]

[0607]

[0608] As shown in Table 1 above, Examples 1-1 to 1-14 of organic light-emitting devices, which use compounds of chemical formulas 1 to 6 of this specification together as the host and dopant of the organic light-emitting device, exhibit excellent characteristics in terms of efficiency, driving voltage and stability.

[0609] In particular, Comparative Examples 1-1 and 1-2 used only one host material, and Comparative Examples 1-5 and 1-6 used only one dopant material. Compared with Examples 1-1 to 1-14, which used two compounds as host materials and two compounds as dopant materials, they showed reduced performance, particularly reduced efficiency and reduced lifetime.

[0610] Comparative Examples 1-3, 1-4, and 1-7 used iridium dopants and large platinum dopants, which, compared with Examples 1-1 to 1-14 using platinum dopants and boron dopants of Chemical Formulas 4 to 6 of this application, had higher voltage, lower efficiency, and shorter lifetime, with particularly reduced efficiency and lifetime.

Claims

1. An organic light-emitting device, wherein, include: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more layers disposed between the first electrode and the second electrode. The organic layer includes a light-emitting layer comprising a first host compound represented by chemical formula 1 or 2, a second host compound represented by chemical formula 3, a first dopant compound represented by chemical formula 4 or 5, and a second dopant compound represented by chemical formula 6. [Chemical Formula 1] [Chemical Formula 2] In the chemical formulas 1 and 2, R1 to R6 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. R1 to R3 and L1 can combine with adjacent substituents to form a ring. R4 to R6 and L2 can combine with adjacent substituents to form a ring. R21 to R24 may be the same as or different from each other, and each is independently a hydrogen, deuterium, nitrile, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. R25 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. L1 and L2 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. a1 is an integer from 1 to 8. a2 to a4 are each integers from 1 to 7. When each of a1 to a4 has more than 2 substituents, the substituents within the parentheses may be the same or different from each other. [Chemical Formula 3] In the chemical formula 3, X1 to X3 may be the same as or different from each other, and each can be N or CR independently. R can be hydrogen, deuterium, nitrile, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkenyl, or substituted or unsubstituted heteroaryl. HET is a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted heteroaryl group. R7 to R9 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. R26 is hydrogen, deuterium, nitrile, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. When a6 is an integer from 1 to 8, and a6 is 2 or higher, R26 may be the same or different from each other. L3 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. [Chemical Formula 4] [Chemical Formula 5] In chemical formulas 4 and 5, M is a transition metal. Z1 is a substituted or unsubstituted N-containing monocyclic or bicyclic heterocycle. R11 and R12 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. R13 to R16, R18 to R20, and R35 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, nitrile, halogen, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted boryl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. a, b, e, and f are each integers from 1 to 3. c, d, g, and h are each integers from 1 to 4. a5 is 1 or 2. When a to h are complex numbers, the substituents within the parentheses may be the same or different from each other. When a5 is 2, R35 may be the same or different from each other. [Chemical Formula 6] In the chemical formula 6, A1 to A3 may be the same as or different from each other, and each may be an independently substituted or unsubstituted heterocycle or a substituted or unsubstituted hydrocarbon ring. B1 and B2 may be the same as or different from each other, and each may be a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted hydrocarbon cyclic group.

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 Formulas 1-3] [Chemical Formulas 1-4] In the chemical formulas 1-1 to 1-4, the definitions of R1 to R3, L1, R21, R22, a1, and a2 are the same as those in chemical formula 1.

3. The organic light-emitting device according to claim 1, wherein, Chemical formula 2 is represented by any one of the following chemical formulas 2-1 to 2-16: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6] [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9] [Chemical Formula 2-10] [Chemical Formula 2-11] [Chemical Formula 2-12] [Chemical Formula 2-13] [Chemical Formula 2-14] [Chemical Formula 2-15] [Chemical Formula 2-16] In the chemical formulas 2-1 to 2-16, the definitions of R4 to R6, L2, R23 to R25, a3 and a4 are the same as those in chemical formula 2.

4. The organic light-emitting device according to claim 1, wherein, The HET is carbazolyl, dibenzofuranyl, or dibenzothiophenel.

5. The organic light-emitting device according to claim 1, wherein, R1 to R9 may be the same as or different from each other, and each is independently a phenyl group.

6. The organic light-emitting device according to claim 1, wherein, R11 and R12 are methyl groups.

7. The organic light-emitting device according to claim 1, wherein, M is Pt.

8. The organic light-emitting device according to claim 1, wherein, The first dopant compound represented by the chemical formula 4 or 5 is a phosphorescent dopant compound.

9. The organic light-emitting device according to claim 1, wherein, The second dopant compound represented by the chemical formula 6 is a fluorescent dopant compound.

10. The organic light-emitting device according to claim 1, wherein, The chemical formula 1 is any one of the following compounds:

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

12. The organic light-emitting device according to claim 1, wherein, The chemical formula 3 is any one of the following compounds:

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

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

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

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