Compounds and organic light emitting devices comprising the same

Abstract

The present specification relates to compounds of Chemical Formula 1 and organic light emitting devices comprising the same.

Description

Compounds and organic light-emitting devices containing them Technical Field

[0001]

[0002] This application claims priority to Korean Patent Application No. 10-2020-0092271, filed with the Korean Intellectual Property Office on July 24, 2020, the entire contents of which are incorporated herein by reference.

[0003] This specification relates to compounds and organic light-emitting devices containing them. Background Technology

[0004]

[0005] 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.

[0006] There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the Invention

[0007]

[0008] Technical issues

[0009] This specification provides compounds and organic light-emitting devices containing them.

[0010] Solution to the problem

[0011] One embodiment of this specification provides a compound represented by the following chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] X1 is either O or S.

[0016] At least one of Y1 to Y5 is N, and the rest are each independently CR3.

[0017] R1 and R2 may be the same or different from each other, and each may be independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0018] R3 can be hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl containing a six-membered ring containing N, or substituted or unsubstituted heteroaryl containing O or S, or can combine with adjacent groups to form substituted or unsubstituted rings.

[0019] L1 is a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0020] l1 is an integer from 1 to 5.

[0021] m is 1 or 2

[0022] n is an integer from 1 to 4.

[0023] When there are 2 or more L1 values, the 2 or more L1 values ​​are either the same or different from each other.

[0024] When n is 2 or more, the above 2 or more Whether they are the same or different,

[0025] This indicates the site where L1 combines with chemical formula 1.

[0026] In addition, one embodiment of this specification provides an organic light-emitting device, which 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 aforementioned compound.

[0027] Invention Effects

[0028] The compound according to one embodiment of this specification can be used as a material for the organic layer of an organic light-emitting device, thereby enabling improved efficiency, lower driving voltage, and / or improved lifetime characteristics in the organic light-emitting device. Attached Figure Description

[0029]

[0030] Figures 1 and 2 illustrate examples of organic light-emitting devices according to one embodiment of this specification.

[0031] [Symbol Explanation]

[0032] 101: Substrate

[0033] 102: First electrode

[0034] 111: Organic layer

[0035] 110: Second electrode

[0036] 103: Hole Injection Layer

[0037] 104: Hole Transport Layer

[0038] 105: Emissive layer

[0039] 106: Electron Injection and Transport Layer Detailed Implementation

[0040]

[0041] The following is a more detailed description of this instruction manual.

[0042] This specification provides for compounds represented by the above chemical formula 1.

[0043] According to one embodiment of this specification, chemical formula 1 is a structure in which a cyano group and an N-containing monocyclic heterocyclic derivative substituent are respectively bonded to a thiol or thiolium core. Including such a structure in the organic layer of an organic light-emitting device enables improved efficiency, lower driving voltage, and improved lifetime characteristics.

[0044] Specifically, the N-containing heterocyclic derivatives and cyano groups of the above-mentioned chemical formula 1 have an electron-depleted structure, which can increase the polarity (dipole moment) of the molecule. Therefore, when fabricating organic light-emitting devices containing compounds represented by the above-mentioned chemical formula 1, the electron mobility can be smoothly adjusted, thereby improving the efficiency and lifetime of organic light-emitting devices containing compounds represented by the above-mentioned chemical formula 1.

[0045] Furthermore, the steric barrier caused by the xatonium and thiotonium structures of the compounds of Formula 1 prevents crystallization during film formation, maintaining high thermal stability and exhibiting excellent stability even at high evaporation temperatures. Therefore, organic light-emitting devices comprising the compounds according to one embodiment of this specification can achieve improved efficiency, lower driving voltage, and improved lifetime characteristics.

[0046] Examples of substituents in this specification are described below, but are not limited thereto.

[0047] In this instruction manual, Indicates the part that is connected.

[0048] 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.

[0049] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen group, cyano, alkyl, cycloalkyl, alkoxy, alkenyl, haloalkyl, silyl, boron, amino, aryl and heteroaryl, or substituted by two or more substituents linked together from the substituents exemplified above, or not having any substituents.

[0050] In this specification, "two or more substituents linked" means that the hydrogen of any one substituent is linked to other substituents. For example, two substituents linked is a phenyl group linked to a naphthyl group, which can form... Such substituents. Furthermore, the connection of three substituents not only includes a sequential connection of (substituent 1)-(substituent 2)-(substituent 3), but also includes (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl, and isopropyl can be linked to form... Such substituents. The same definition applies to connections of four or more substituents.

[0051] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0052] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0053] In this specification, cycloalkyl groups are not particularly limited, but preferably cycloalkyl groups with 3 to 30 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, adamantyl, etc., but are not limited to these.

[0054] 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, it can be methoxy, ethoxy, n-propoxy, isopropoxy, 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.

[0055] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc., but are not limited to these.

[0056] In this specification, the above-mentioned haloalkyl refers to a hydrogen atom that has been replaced by at least one halogen group instead of the alkyl group defined above.

[0057] In this specification, aryl is not particularly limited, but it is preferred to be an aryl with 6 to 30 carbon atoms, and the aryl can be monocyclic or polycyclic.

[0058] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferred to have 6 to 30 carbon atoms. Specifically, the monocyclic aryl group can be phenyl, biphenyl, terphenyl, etc., but is not limited to these.

[0059] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferred to have 10 to 30 carbon atoms. Specifically, the polycyclic aryl group can be naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, beryl, perylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0060] In this specification, the fluorene group can be substituted, and adjacent groups can combine with each other to form a ring.

[0061] When the aforementioned fluorene group is replaced, there is

[0062] etc., but not limited to this.

[0063] 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.

[0064] 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 is preferably 2 to 30. The heteroaryl group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, 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, phenanthridine, phenanthroline, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phen Thiol (phenoxathiine), phen Phenoxazine, phenothiazine, dihydroindocarbazolyl, spirofluorenyloxetyl, and spirofluorenylthioxetyl are examples, but not limited to these.

[0065] In this specification, the aforementioned silane group can be alkylsilane, arylsilane, heteroarylsilane, etc. The alkyl group in the aforementioned alkylsilane can be any of the examples of the aforementioned alkyl groups; the aryl group in the aforementioned arylsilane can be any of the examples of the aforementioned aryl groups; and the heteroaryl group in the aforementioned heteroarylsilane can be any of the examples of the aforementioned heteroaryl groups.

[0066] In this specification, the boron group can be -BR 100 R 101 The above R 100 and R 101Whether the groups are the same or different, they can be independently selected from hydrogen, deuterium, halogen, nitrile, cyclic alkyl groups with 3 to 30 substituted or unsubstituted carbon atoms (monocyclic or polycyclic), straight-chain or branched alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms (monocyclic or polycyclic), aryl groups with 6 to 30 substituted or unsubstituted carbon atoms (monocyclic or polycyclic), and heteroaryl groups with 2 to 30 substituted or unsubstituted carbon atoms (monocyclic or polycyclic). Specific examples of the aforementioned boryl groups include dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, etc., but are not limited to these.

[0067] 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-methyl-anthraylamino, diphenylamino, 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.

[0068] In this specification, N-alkylarylamine refers to an amino group in which an alkyl or aryl group is substituted for the N group. The alkyl and aryl groups in the above-described N-alkylarylamine are the same as those exemplified above.

[0069] In this specification, N-arylheteroarylamine refers to an amino group in which an aryl or heteroaryl group is substituted at the N atom of the amino group. The aryl and heteroaryl groups in the above-described N-arylheteroarylamine are the same as those exemplified above.

[0070] In this specification, N-alkylheteroarylamine refers to an amino group in which an alkyl or heteroaryl group is substituted for the N group. The alkyl and heteroaryl groups in the above-described N-alkylheteroarylamine are the same as those exemplified above.

[0071] In this specification, examples of arylamines include substituted or unsubstituted monoarylamines and substituted or unsubstituted diarylamines. Arylamines containing two or more of the above-described aryl groups may include monocyclic aryl, polycyclic aryl, or both. For example, the aryl groups in the above-described arylamines may be selected from the examples of the aryl groups described above.

[0072] In this specification, examples of heteroarylamines include substituted or unsubstituted mono-heteroarylamines and substituted or unsubstituted di-heteroarylamines. Heteroarylamines containing two or more of the above-mentioned heteroaryl groups may include monocyclic heteroaryl, polycyclic heteroaryl, or both. For example, the heteroaryl groups in the above-mentioned heteroarylamines may be selected from the examples of heteroaryl groups described above.

[0073] In this specification, "adjacent groups combine with each other to form a ring" in the context of substituents means that they combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle.

[0074] In this specification, in the context of substituted or unsubstituted rings formed by their combination, "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle.

[0075] In this specification, the hydrocarbon ring can be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and can be selected from the examples of the above-mentioned cycloalkyl or aryl groups, except that it is not monovalent as described above.

[0076] 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 may be selected from the examples of the heteroaryl groups mentioned above, except that they are not monovalent.

[0077] 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, oxepane Azahexacyclic octane Thioheterocyclic octane etc., but not limited to this.

[0078] In this specification, arylene refers to a group with two bonding sites on an aryl group, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the above description of aryl groups.

[0079] In this specification, a heteroaryl group refers to a group with two bonding sites on a heteroaryl group, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the above description of heteroaryl groups.

[0080] The compounds represented by the above chemical formula 1 will now be described in detail.

[0081] According to one embodiment of this specification, X1 is 0.

[0082] According to one embodiment of this specification, X1 is S.

[0083] According to one embodiment of this specification, the above chemical formula 1 is represented by the following chemical formula 2 or 3.

[0084] [Chemical Formula 2]

[0085]

[0086] [Chemical Formula 3]

[0087]

[0088] In the above chemical formulas 2 and 3,

[0089] R1, R2, Y1 to Y5, L1, l1, m, and n are the same as defined in Chemical Formula 1 above. According to one embodiment of this specification, m is 1.

[0090] According to one embodiment of this specification, m is 2.

[0091] According to one embodiment of this specification, n is 1.

[0092] According to one embodiment of this specification, n is 2.

[0093] According to one embodiment of this specification, n is 3.

[0094] According to one embodiment of this specification, n is 4.

[0095] According to one embodiment of this specification, the above chemical formula 1 is represented by the following chemical formula 4 or 5.

[0096] [Chemical Formula 4]

[0097]

[0098] [Chemical Formula 5]

[0099]

[0100] In the above chemical formulas 4 and 5,

[0101] X1, R1, R2, Y1 to Y5, L1 and l1 are the same as those defined in the above chemical formula 1.

[0102] According to one embodiment of this specification, the above chemical formula 1 is represented by any one of the following chemical formulas 6 to 9.

[0103] [Chemical Formula 6]

[0104]

[0105] [Chemical Formula 7]

[0106]

[0107] [Chemical Formula 8]

[0108]

[0109] [Chemical Formula 9]

[0110]

[0111] In the above chemical formulas 6 to 9,

[0112] R1, R2, Y1 to Y5, L1 and l1 are the same as those defined in Chemical Formula 1 above.

[0113] According to one embodiment of this specification, l1 is 1.

[0114] According to one embodiment of this specification, l1 is 2.

[0115] According to one embodiment of this specification, l1 is 3.

[0116] In this specification, when l1 is 2 or more in the above chemical formula 1, two or more L1s are the same or different from each other, and it indicates that each L1 is connected in a straight chain. For example, when l1 is 3 and L1s are phenylene, naphthylene and phenylene respectively, they can be connected as follows, but are not limited thereto, and the order or connection position of each L1 can be different.

[0117]

[0118] Additionally, for example, when l1 is 3, it represents the above chemical formula 1. It combines with the phenylene group at the third position in the structure illustrated above.

[0119] According to one embodiment of this specification, at least two of Y1 to Y5 are N, and the rest are each independently CR3.

[0120] According to one embodiment of this specification, at least three of Y1 to Y5 are N, and the rest are each independently CR3.

[0121] According to one embodiment of this specification, any one of Y1 to Y5 is N, and the rest are each independently CR3.

[0122] According to one embodiment of this specification, any two of Y1 to Y5 are N, and the rest are each independently CR3.

[0123] According to one embodiment of this specification, any three of Y1 to Y5 are N, and the rest are each independently CR3.

[0124] According to one embodiment of this specification, Y1 is N, Y2 to Y5 are the same as or different from each other, and each is independently CR3.

[0125] According to one embodiment of this specification, Y2 is N, Y1 and Y3 to Y5 are the same or different from each other, and each is independently CR3.

[0126] According to one embodiment of this specification, Y3 is N, and Y1, Y2, Y4 and Y5 are the same or different from each other, and each is independently CR3.

[0127] According to one embodiment of this specification, Y1 and Y5 are N, Y2 to Y4 are the same as or different from each other, and each is independently CR3.

[0128] According to one embodiment of this specification, Y1 and Y3 are N, Y2, Y4 and Y5 are the same or different from each other, and each is independently CR3.

[0129] According to one embodiment of this specification, Y2 and Y4 are N, Y1, Y3 and Y5 are the same as or different from each other, and each is independently CR3.

[0130] According to one embodiment of this specification, Y3 and Y5 are N, Y1, Y2 and Y4 are the same as or different from each other, and each is independently CR3.

[0131] According to one embodiment of this specification, Y1 and Y2 are N, Y3 to Y5 are the same as or different from each other, and each is independently CR3.

[0132] According to one embodiment of this specification, Y4 and Y5 are N, Y1 to Y3 are the same as or different from each other, and each is independently CR3.

[0133] According to one embodiment of this specification, Y2 and Y3 are N, Y1, Y4 and Y5 are the same as or different from each other, and each is independently CR3.

[0134] According to one embodiment of this specification, Y3 and Y4 are N, Y1, Y2 and Y5 are the same as or different from each other, and each is independently CR3.

[0135] According to one embodiment of this specification, Y1 and Y4 are N, Y2, Y3 and Y5 are the same or different from each other, and each is independently CR3.

[0136] According to one embodiment of this specification, Y2 and Y5 are N, Y1, Y3 and Y4 are the same as or different from each other, and each is independently CR3.

[0137] According to one embodiment of this specification, Y1, Y3 and Y5 are N, Y2 and Y4 are the same as or different from each other, and each is independently CR3.

[0138] According to one embodiment of this specification, the above It is selected from any of the following structures.

[0139]

[0140] In the above structure,

[0141] R31 to R35 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or may combine with adjacent groups to form substituted or unsubstituted rings.

[0142] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.

[0143] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroaryl group with 2 to 20 substituted or unsubstituted carbon atoms.

[0144] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 10 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroaryl group with 2 to 15 substituted or unsubstituted carbon atoms.

[0145] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0146] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

[0147] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 15 carbon atoms.

[0148] According to one embodiment of this specification, R1 and R2 are phenyl, naphthyl, pyridyl, dibenzofuranyl, or dibenzothiophene.

[0149] According to one embodiment of this specification, R3 is hydrogen, deuterium, a straight-chain or branched alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic heteroaryl group with 2 to 30 substituted carbon atoms containing a six-membered ring with N, or a monocyclic or polycyclic heteroaryl group with 2 to 30 substituted carbon atoms containing O or S, or can be combined with adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 substituted carbon atoms, or a monocyclic or polycyclic heterocycle with 2 to 30 substituted carbon atoms.

[0150] According to one embodiment of this specification, R3 is hydrogen, deuterium, a straight-chain or branched alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic heteroaryl group with 2 to 20 substituted carbon atoms containing a six-membered ring with N, or a monocyclic or polycyclic heteroaryl group with 2 to 20 substituted carbon atoms containing O or S, or can be combined with adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 20 substituted carbon atoms, or a monocyclic or polycyclic heterocycle with 2 to 20 substituted carbon atoms.

[0151] According to one embodiment of this specification, R3 is hydrogen; deuterium; a straight-chain or branched alkyl group having 1 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms that is substituted with or unsubstituted with a cyano group, or a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms that is substituted with or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms that contains a six-membered ring containing N; or a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms that contains O or S; or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms that can combine with adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

[0152] According to one embodiment of this specification, R3 is hydrogen, deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted with a cyano-substituted or unsubstituted alkyl group, or a monocyclic or polycyclic aryl group having 1 to 30 carbon atoms substituted with a straight-chain or branched alkyl group, or an unsubstituted alkyl group. A heteroaryl group consisting of a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a heteroaryl group consisting of a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms containing a six-membered ring with N, or a heteroaryl group consisting of a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms containing O or S, or a heterocyclic aryl group that can combine with adjacent groups to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a monocyclic or polycyclic aryl ring having 2 to 30 carbon atoms.

[0153] According to one embodiment of this specification, R3 is hydrogen; deuterium; a straight-chain or branched alkyl group having 1 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms that is substituted with or unsubstituted with a cyano group, or a monocyclic or polycyclic aryl group having 2 to 20 carbon atoms that is substituted with or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; a monocyclic or polycyclic aryl group having 2 to 20 carbon atoms that contains a six-membered ring containing N; or a monocyclic or polycyclic aryl group having 2 to 20 carbon atoms that contains O or S; or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms that can combine with adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.

[0154] According to one embodiment of this specification, R3 is hydrogen; deuterium; methyl; pyridyl group substituted with cyano, methyl-substituted or unsubstituted, naphthyl group substituted with cyano, or phenanthrene-substituted or unsubstituted; pyridyl; phenanthrene; naphthyl group substituted with cyano, or unsubstituted; biphenyl group substituted with cyano, or unsubstituted; fluoranthyl; dibenzofuranyl or dibenzothiophenyl, or may combine with adjacent groups to form benzene or benzofuran.

[0155] According to one embodiment of this specification, R31 to R35 may be the same as or different from each other, and each independently comprises hydrogen, deuterium, a straight-chain or branched alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic heteroaryl group with 2 to 30 substituted carbon atoms containing a six-membered ring containing N, or a monocyclic or polycyclic heteroaryl group with 2 to 30 substituted carbon atoms containing O or S, or may combine with adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 substituted carbon atoms, or a monocyclic or polycyclic heterocycle with 2 to 30 substituted carbon atoms.

[0156] According to one embodiment of this specification, R31 to R35 may be the same as or different from each other, and each independently comprises hydrogen, deuterium, a straight-chain or branched alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic heteroaryl group with 2 to 20 substituted carbon atoms containing a six-membered ring containing N, or a monocyclic or polycyclic heteroaryl group with 2 to 20 substituted carbon atoms containing O or S, or may combine with adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 20 substituted carbon atoms, or a monocyclic or polycyclic heterocycle with 2 to 20 substituted carbon atoms.

[0157] According to one embodiment of this specification, R31 to R35 may be the same as or different from each other, and each independently represents hydrogen; deuterium; a straight-chain or branched alkyl group having 1 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms that is substituted with or unsubstituted with a cyano group, or a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms that is substituted with or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms that contains a six-membered ring containing N; or a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms that contains O or S; or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, which can be combined with adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

[0158] According to one embodiment of this specification, R31 to R35 may be the same as or different from each other, and each independently comprises hydrogen, deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted with a cyano-substituted or unsubstituted aryl group, or a straight-chain or branched aryl group having 1 to 30 carbon atoms. The aryl group having alkyl-substituted or unsubstituted chains, comprising a monocyclic or polycyclic aromatic hydrocarbon ring having 2 to 30 carbon atoms, comprising a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, comprising a monocyclic or polycyclic aromatic hydrocarbon ring having 2 to 30 carbon atoms containing a six-membered ring containing N, comprising a monocyclic or polycyclic aromatic hydrocarbon ring having 2 to 30 carbon atoms containing O or S, or which can combine with adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

[0159] According to one embodiment of this specification, R31 to R35 may be the same as or different from each other, and each independently represents hydrogen; deuterium; a straight-chain or branched alkyl group having 1 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms that is substituted with or unsubstituted with a cyano group, or a monocyclic or polycyclic aryl group having 2 to 20 carbon atoms that is substituted with or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; a monocyclic or polycyclic aryl group having 2 to 20 carbon atoms that contains a six-membered ring containing N; or a monocyclic or polycyclic aryl group having 2 to 20 carbon atoms that contains O or S; or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms that can be combined with adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.

[0160] According to one embodiment of this specification, R31 to R35 may be the same as or different from each other, and each independently represents hydrogen; deuterium; methyl; pyridyl group substituted with cyano, substituted with methyl or unsubstituted, naphthyl group substituted with cyano or unsubstituted, or phenyl group substituted with phenanthrene or unsubstituted; pyridyl; phenanthrene; naphthyl group substituted with cyano or unsubstituted; biphenyl group substituted with cyano or unsubstituted; fluoranyl; dibenzofuranyl or dibenzothiophenyl, or may combine with adjacent groups to form benzene or benzofuran.

[0161] According to one embodiment of this specification, the above It is selected from any of the following structures.

[0162]

[0163] In the above structure,

[0164] The definitions of R31 to R35 are the same as those above.

[0165] According to one embodiment of this specification, L1 is a monocyclic or polycyclic arylene with 6 to 30 carbon atoms that is directly bonded, substituted or unsubstituted, or a monocyclic or polycyclic heteroarylene with 2 to 30 carbon atoms that is substituted or unsubstituted.

[0166] According to one embodiment of this specification, L1 is a monocyclic or polycyclic arylene with 6 to 20 carbon atoms that is directly bonded, substituted or unsubstituted, or a monocyclic or polycyclic heteroarylene with 2 to 20 carbon atoms that is substituted or unsubstituted.

[0167] According to one embodiment of this specification, L1 is a directly bonded monocyclic or polycyclic arylene with 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 30 carbon atoms.

[0168] According to one embodiment of this specification, L1 is a directly bonded monocyclic or polycyclic arylene with 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 20 carbon atoms.

[0169] According to one embodiment of this specification, L1 is a directly bonded, phenylene, biphenylene, naphthylene, terphenylene, divalent pyridyl, divalent dibenzofuranyl, or divalent dibenzothiophene.

[0170] According to one embodiment of this specification, R1 and R2 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 monocyclic or polycyclic heteroaryl group with 2 to 30 carbon atoms.

[0171] R3 above is hydrogen; deuterium; a straight-chain or branched alkyl group having 1 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms that is substituted with or unsubstituted with a cyano group, or a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms that is substituted with or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms that can be combined with adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms; L1 above is a directly bonded monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

[0172] According to one embodiment of this specification, the above-mentioned chemical formula 1 is any one selected from the following compounds and the compounds listed in Tables 1 to 12 below.

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180] [Table 1]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] [Table 2]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222] [Table 3]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241] [Table 4]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259] [Table 5]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277] [Table 6]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298] [Table 7]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306] [Table 8]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322] [Table 9]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340] [Table 10]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357] [Table 11]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376] [Table 12]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396] In Tables 1 to 12 above,

[0397] * represents chemical formula 1 above. With the above chemical formula 1 The joint area,

[0398] The above chemical formula 1 represents With the above chemical formula 1 The site of connection.

[0399] This specification provides an organic light-emitting device comprising a compound represented by the above chemical formula 1.

[0400] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0401] In this specification, when a part is indicated to "include / comprise" a certain element, unless otherwise stated, it means that other elements may be included, rather than excluding other elements.

[0402] In this specification, the term "layer" is used interchangeably with "film" primarily used in this technical field, referring to a coating covering a target area. The size of the "layer" is not limited; the sizes of individual "layers" can be the same or different. According to one embodiment, the size of a "layer" can be equal to the size of the entire device, equivalent to the size of a specific functional area, or as small as a single sub-pixel.

[0403] In this specification, the meaning of a specific substance A being contained in layer B includes i) the case where one or more substances A are contained in a single layer of layer B, and ii) the case where layer B consists of one or more layers and substances A are contained in one or more layers of multiple layers of layer B.

[0404] In this specification, the meaning of a specific substance A being contained in layer C or layer D includes all cases where it is contained in layer C or more than one layer, or in layer D or more than one layer, or in layers C or D or more than one layer respectively.

[0405] This specification 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, wherein one or more of the organic layers comprises a compound represented by the above chemical formula 1.

[0406] The organic layers of the organic light-emitting device described in this specification 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, it can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. However, the structure of the organic light-emitting device is not limited to this and can include fewer organic layers.

[0407] According to one embodiment of this specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, wherein the electron injection layer, electron transport layer, or electron injection and transport layer contains the aforementioned compound.

[0408] According to one embodiment of this specification, the organic layer includes a hole-blocking layer, and the hole-blocking layer contains the aforementioned compound.

[0409] According to one embodiment of this specification, the aforementioned organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, wherein the aforementioned hole injection layer, hole transport layer, or hole injection and transport layer contains the aforementioned compound.

[0410] According to one embodiment of this specification, the organic layer includes a light-emitting layer.

[0411] According to one embodiment of this specification, the aforementioned organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.

[0412] According to one embodiment of this specification, the organic layer includes an electron blocking layer.

[0413] According to one embodiment of this specification, the organic layer includes a hole-blocking layer.

[0414] According to one embodiment of this specification, the above-mentioned organic light-emitting device further includes one or more layers selected from hole injection layer, hole transport layer, hole injection and transport layer, light-emitting layer, electron transport layer, electron injection layer, electron injection and transport layer, hole blocking layer, and electron blocking layer.

[0415] According to one embodiment of this specification, the organic light-emitting device includes: a first electrode; a second electrode disposed opposite to the first electrode; a light-emitting layer disposed between the first electrode and the second electrode; and two or more organic layers disposed between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0416] According to one embodiment of this specification, the above-mentioned two or more organic layers may be selected from two or more of the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0417] According to one embodiment of this specification, two or more hole transport layers are included between the light-emitting layer and the first electrode. These two or more hole transport layers may contain the same or different materials.

[0418] According to one embodiment of this specification, the first electrode is an anode or a cathode.

[0419] According to one embodiment of this specification, the second electrode is a cathode or an anode.

[0420] According to one embodiment of this specification, the above-mentioned organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0421] According to one embodiment of this specification, the organic light-emitting device can be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0422] For example, the structure of an organic light-emitting device according to one embodiment of this specification is illustrated in Figures 1 and 2. Figures 1 and 2 illustrate organic light-emitting devices, but are not limited thereto.

[0423] Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode 102, an organic layer 111, and a second electrode 110 are sequentially stacked on a substrate 101. The compound represented by the above-described chemical formula 1 is contained in the organic layer.

[0424] Figure 2 illustrates the structure of an organic light-emitting device in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light-emitting layer 105, an electron injection and transport layer 106, and a second electrode 110 are sequentially stacked on a substrate 101. The compound represented by the above-described chemical formula 1 is contained in the electron injection and transport layer.

[0425] The organic light-emitting devices described in this specification, except that the electron injection layer, electron transport layer, electron injection and transport layer, hole injection layer, hole transport layer, hole injection and transport layer, or hole blocking layer contains the above-mentioned compounds, i.e., compounds represented by the above-mentioned chemical formula 1, can be manufactured using materials and methods known in the art.

[0426] In the case where the above-mentioned organic light-emitting device includes a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0427] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; then forming an organic layer on the anode, comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer; and finally depositing a material suitable for use as a cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0428] Furthermore, the compound represented by the above chemical formula 1 can be used to form an organic layer in the manufacture of organic light-emitting devices not only by vacuum evaporation but also by solution coating. Here, solution coating refers to methods such as spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roller coating, but is not limited to these.

[0429] In addition to these methods, organic light-emitting devices can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. However, the manufacturing method is not limited to these methods.

[0430] As the aforementioned anode material, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. For example, 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-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but not limited to these.

[0431] As the cathode material mentioned above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer materials such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0432] The aforementioned luminescent layer may comprise a host material and a dopant material. The host material may be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include dibenzofuran derivatives and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited to these.

[0433] According to one embodiment of this specification, the above-mentioned body comprises, but is not limited to, a compound represented by the following chemical formula H-1.

[0434] [Chemical formula H-1]

[0435]

[0436] In the above chemical formula H-1,

[0437] L20 and L21 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0438] Ar20 and Ar21 may be the same as or different from each other, and each can be independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0439] R201 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0440] r201 is an integer from 1 to 8. When r201 is 2 or more, two or more r201s are the same or different from each other.

[0441] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each is independently a directly bonded monocyclic or polycyclic arylene group with 6 to 30 carbon atoms, or a divalent heterocyclic group with 2 to 30 carbon atoms.

[0442] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each independently is a directly bonded, deuterated or unsubstituted phenylene, deuterated or unsubstituted biphenylene, deuterated or unsubstituted naphthylene, divalent dibenzofuranyl or divalent dibenzothiophene.

[0443] In one embodiment of this specification, the Ar20 and Ar21 described above 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 that has been substituted or unsubstituted, or a monocyclic or polycyclic heterocyclic group with 2 to 30 carbon atoms that has been substituted or unsubstituted.

[0444] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each is independently a monocyclic to tetracyclic aryl group with 6 to 20 carbon atoms, substituted or unsubstituted, or a monocyclic to tetracyclic heterocyclic group with 6 to 20 carbon atoms.

[0445] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. The aryl-substituted or unsubstituted thiophene group; the dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; the naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; the dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or the naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0446] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each independently represents a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a terphenyl, a deuterated or unsubstituted naphthyl, a phenyl-substituted or unsubstituted thiophene, a phenanthryl, a dibenzofuranyl, a naphthobenzofuranyl, a dibenzothiophene, or a naphthobenzothiophene.

[0447] In one embodiment of this specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0448] According to one embodiment of this specification, R201 is hydrogen.

[0449] According to one embodiment of this specification, the above chemical formula H-1 is represented by the following compound.

[0450]

[0451] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives with substituted or unsubstituted aryl amine groups, such as pyrene, anthracene, etc., which have aryl amine groups. Diindrone pyrene, etc. Furthermore, styrylamine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., but they are not limited to these. Furthermore, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these.

[0452] According to one embodiment of this specification, the dopant comprises, but is not limited to, a compound represented by the following chemical formula D-1.

[0453] [Chemical Formula D-1]

[0454]

[0455] In the above chemical formula D-1,

[0456] T1 to T6 may be the same as or different from each other, and each is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0457] t5 and t6 are each integers from 1 to 4.

[0458] When t5 is 2 or more, the two or more T5 values ​​are either the same or different from each other.

[0459] When t6 is 2 or more, the two or more T6 are the same or different from each other.

[0460] According to one embodiment of this specification, T1 to T6 may be the same as or different from each other, and each is independently hydrogen, a straight-chain or branched alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.

[0461] According to one embodiment of this specification, T1 to T6 may be the same as or different from each other, and each is independently hydrogen; a straight-chain or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted with or unsubstituted with a cyano group or a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0462] According to one embodiment of this specification, T1 to T6 may be the same as or different from each other, and each is independently hydrogen, isopropyl, phenyl substituted with cyano, or phenyl substituted with methyl.

[0463] According to one embodiment of this specification, the above chemical formula D-1 is represented by the following compound.

[0464]

[0465] The aforementioned hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, the effect of receiving holes from the anode, and an excellent hole injection effect on the light-emitting layer or light-emitting material. Furthermore, it is preferably a material with excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material. Moreover, it is preferably a material with excellent thin film forming ability. Furthermore, it is preferable that 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, polyaniline, and polythiophene-based conductive polymers.

[0466] 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-1.

[0467] [Chemical formula HI-1]

[0468]

[0469] In the above chemical formula HI-1,

[0470] R300 to R308 may be the same as or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or may be combined with adjacent groups to form substituted or unsubstituted rings.

[0471] r301 and r302 are each integers from 1 to 4.

[0472] r303 and r304 are each integers from 1 to 3.

[0473] When r301 is 2 or more, the above R301s may be the same or different from each other.

[0474] When r302 is 2 or more, the above R302 may be the same as or different from each other.

[0475] When r303 is 2 or more, the above R303 values ​​may be the same or different from each other.

[0476] When the number of r304 is 2 or more, the above R304s may be the same or different from each other.

[0477] According to one embodiment of this specification, R301 to R304 are hydrogen.

[0478] According to one embodiment of this specification, R300 is a substituted or unsubstituted aryl group.

[0479] According to one embodiment of this specification, R300 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0480] According to one embodiment of this specification, R300 is a phenyl group.

[0481] According to one embodiment of this specification, R305 to R308 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.

[0482] According to one embodiment of this specification, R305 to R308 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 monocyclic or polycyclic heteroaryl group with 2 to 30 carbon atoms substituted or unsubstituted by a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms.

[0483] According to one embodiment of this specification, R305 to R308 may be the same as or different from each other, and each is independently a phenyl group, or a carbazolyl group substituted with or unsubstituted with a phenyl group.

[0484] According to one embodiment of this specification, the above chemical formula HI-1 is represented by the following compound.

[0485]

[0486] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a substance capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer, and is preferably a substance with a high hole mobility. Specific examples include arylamine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0487] 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.

[0488] [Chemical formula HT-1]

[0489]

[0490] In the above chemical formula HT-1,

[0491] At least one of X'1 to X'6 is N, and the rest are CH.

[0492] R309 to R314 may be the same as or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or combined with adjacent groups to form substituted or unsubstituted rings.

[0493] According to one embodiment of this specification, X'1 to X'6 are N.

[0494] According to one embodiment of this specification, R309 to R314 are cyano groups.

[0495] According to one embodiment of this specification, the above-mentioned chemical formula HT-1 is represented by the following compound.

[0496]

[0497] 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-2.

[0498] [Chemical formula HT-2]

[0499]

[0500] In the above chemical formula HT-2,

[0501] R315 to R317 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 heteroaryl, and combinations thereof, or may be combined with adjacent groups to form substituted or unsubstituted rings.

[0502] r315 is an integer from 1 to 5. When r315 is 2 or more, two or more of the above R315 are either the same or different from each other.

[0503] r316 is an integer from 1 to 5. When r316 is 2 or more, two or more of the above R316 are the same or different from each other.

[0504] According to one embodiment of this specification, R317 is selected from any one of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, and combinations thereof.

[0505] According to one embodiment of this specification, R317 is selected from carbazolyl, phenyl, biphenyl, and combinations thereof.

[0506] According to one embodiment of this specification, R315 and R316 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.

[0507] According to one embodiment of this specification, R315 and R316 may be the same as or different from each other, each being independently phenyl, or combined with adjacent groups to form methyl-substituted indene.

[0508] According to one embodiment of this specification, the above-mentioned chemical formula HT-2 is represented by the following compound.

[0509]

[0510] The aforementioned electron transport layer is the layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. When an organic light-emitting device according to one embodiment of this specification includes an additional electron transport layer besides the electron transport layer comprising the aforementioned chemical formula 1, the electron transport material is a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, preferably a material with high electron mobility. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, suitable cathode materials are generally materials with low work functions and accompanied by an aluminum or silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, all of which are accompanied by an aluminum or silver layer.

[0511] The aforementioned electron injection layer is a layer that receives electrons from the electrode. When an organic light-emitting device according to one embodiment of this specification includes an additional electron injection layer besides the electron injection layer comprising the aforementioned chemical formula 1, the preferred electron injection material is one that has excellent electron transport capabilities, effectively receives electrons from the second electrode, and has excellent electron injection effects on the light-emitting layer or light-emitting material. Furthermore, it is preferable to use a material that prevents excitons generated in the light-emitting layer from migrating to the hole injection layer and has excellent thin-film formation capabilities. Specifically, this includes fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam 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.

[0512] 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.

[0513] The aforementioned electron blocking layer prevents electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer, thereby improving the device's lifetime and efficiency. It can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport, without limitation using known materials.

[0514] The hole blocking layer described above 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. In an organic light-emitting device according to one embodiment of this specification, when it includes an additional hole blocking layer besides the hole blocking layer comprising the aforementioned chemical formula 1, specifically, there is... Diazole or triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, etc., but not limited to these.

[0515] Depending on the materials used, the organic light-emitting device according to this specification can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0516] The organic light-emitting devices according to this specification can be included in and used in various electronic devices. For example, the aforementioned electronic devices can be display panels, touch panels, solar modules, lighting devices, etc., but are not limited thereto.

[0517] Methods of implementing the invention

[0518] Hereinafter, in order to provide a detailed description of this specification, embodiments and comparative examples will be given. However, various modifications can be made based on the embodiments and comparative examples described herein, and this should not be construed as limiting the scope of this specification to the embodiments and comparative examples detailed below. The embodiments and comparative examples in this specification are provided to provide a more complete explanation of this specification to those skilled in the art.

[0519] [General Formula 1]

[0520]

[0521] The intermediate shown in Manufacturing Example 2 below can be synthesized by the method described in General Formula 1 above.

[0522] Manufacturing Example 1

[0523]

[0524] Compound 1-1a (137.4 g, 296.2 mmol) and zinc cyanide (16.1 g, 137.3 mmol) were added to N,N-dimethylacetamide (1400 mL). TTP (tetrakis(triphenylphosphine)palladium, 9.3 g) was added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was poured into water, and the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 1-1b. (78.9 g, yield 65%, MS: [M+H)) + =410).

[0525] Manufacturing Example 2

[0526]

[0527] Compound 1-1b (80.9 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxab orolane) (55.1 g, 217.0 mmol) were added to 1,4-dioxab orolane. In alkane (600 mL), potassium acetate (58.0 g) and Pd(dppf)Cl2 ([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (4.3 g)) were added, followed by stirring and reflux for 12 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice with ethyl acetate to prepare compound 1-1. (79.1 g, yield 80%, MS: [M+H)) + =502).

[0528] Synthesis example 1

[0529]

[0530] Compound 1-1 (15.0 g, 30 mmol) and compound 1-2 (11.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 1. (14.5 g, yield 71%, MS: [M+H]) + =683).

[0531] Synthesis example 2

[0532]

[0533] Compound 2-1 (14.6 g, 30 mmol) and compound 2-2 (12.2 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 2. (14.1 g, yield 68%, MS: [M+H)) + =692).

[0534] Synthesis example 3

[0535]

[0536] Compound 3-1 (17.7 g, 30 mmol) and compound 3-2 (10.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 3. (16.8 g, yield 75%, MS: [M+H)) + =747).

[0537] Synthesis example 4

[0538]

[0539] Compound 4-1 (14.6 g, 30 mmol) and compound 4-2 (14.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 4. (14.1 g, yield 61%, MS: [M+H)) + =773).

[0540] Synthesis example 5

[0541]

[0542] Compound 5-1 (15.0 g, 30 mmol) and compound 5-2 (14.4 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 5. (16.7 g, yield 72%, MS: [M+H)) + =774).

[0543] Synthesis example 6

[0544]

[0545] Compound 6-1 (14.6 g, 30 mmol) and compound 6-2 (10.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 6. (10.6 g, yield 55%, MS: [M+H)) + =641).

[0546] Synthesis Example 7

[0547]

[0548] Compound 7-1 (15.0 g, 30 mmol) and compound 7-2 (17.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 7. (16.2 g, yield 63%, MS: [M+H)) + =858).

[0549] Synthesis example 8

[0550]

[0551] Compound 8-1 (14.6 g, 30 mmol) and compound 8-2 (13.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 8. (14.5 g, yield 65%, MS: [M+H]) + =742).

[0552] Synthesis example 9

[0553]

[0554] Compound 9-1 (17.7 g, 30 mmol) and compound 9-2 (13.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 9. (19.9 g, yield 78%, MS: [M+H)) + =850).

[0555] Synthesis example 10

[0556]

[0557] Compound 10-1 (14.6 g, 30 mmol) and compound 10-2 (14.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 10. (17.8 g, yield 77%, MS: [M+H)) + =772).

[0558] Synthesis example 11

[0559]

[0560] Compound 11-1 (15.0 g, 30 mmol) and compound 11-2 (13.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 11. (14.6 g, yield 64%, MS: [M+H)) + =759).

[0561] Synthesis example 12

[0562]

[0563] Compound 12-1 (14.6 g, 30 mmol) and compound 12-2 (14.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 12. (16.5 g, yield 71%, MS: [M+H]) + =774).

[0564] Synthesis example 13

[0565]

[0566] Compound 13-1 (14.6 g, 30 mmol) and compound 13-2 (6.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 13. (11.1 g, yield 72%, MS: [M+H)) + =514).

[0567] Synthesis example 14

[0568]

[0569] Compound 14-1 (14.6 g, 30 mmol) and compound 14-2 (12.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 14. (13.5 g, yield 65%, MS: [M+H)) + =693).

[0570] Synthesis Example 15

[0571]

[0572] Compound 15-1 (14.6 g, 30 mmol) and compound 15-2 (15.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 15. (15.0 g, yield 63%, MS: [M+H]) + =794).

[0573] Synthesis example 16

[0574]

[0575] Compound 16-1 (14.6 g, 30 mmol) and compound 16-2 (11.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 16. (14.8 g, yield 74%, MS: [M+H]) + =668).

[0576] Synthesis Example 17

[0577]

[0578] Compound 17-1 (15.0 g, 30 mmol) and compound 17-2 (14.7 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 17. (17.9 g, yield 76%, MS: [M+H]) + =784).

[0579] Synthesis example 18

[0580]

[0581] Compound 18-1 (14.6 g, 30 mmol) and compound 18-2 (13.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 18. (15.1 g, 70% yield, MS: [M+H)) + =717).

[0582] Synthesis example 19

[0583]

[0584] Compound 19-1 (14.6 g, 30 mmol) and compound 19-2 (16.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 19. (17.2 g, 70% yield, MS: [M+H)) + =819).

[0585] Synthesis example 20

[0586]

[0587] Compound 20-1 (16.1 g, 30 mmol) and compound 20-2 (12.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 20. (16.1 g, yield 72%, MS: [M+H)) + =746).

[0588] Synthesis Example 21

[0589]

[0590] Compound 21-1 (15.0 g, 30 mmol) and compound 21-2 (16.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 21. (16.4 g, yield 65%, MS: [M+H)) + =841).

[0591] Synthesis example 22

[0592]

[0593] Compound 22-1 (14.6 g, 30 mmol) and compound 22-2 (11.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 22. (13.8 g, yield 69%, MS: [M+H]) + =668).

[0594] Synthesis example 23

[0595]

[0596] Compound 23-1 (15.0 g, 30 mmol) and compound 23-2 (8.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 23. (12.7 g, yield 73%, MS: [M+H)) + =581).

[0597] Synthesis example 24

[0598]

[0599] Compound 24-1 (14.6 g, 30 mmol) and compound 24-2 (13.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 24. (16.5 g, yield 74%, MS: [M+H]) + =744).

[0600] Synthesis example 25

[0601]

[0602] Compound 25-1 (15.0 g, 30 mmol) and compound 25-2 (15.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 25. (16.7 g, yield 69%, MS: [M+H]) + =808).

[0603] Synthesis Example 26

[0604]

[0605] Compound 26-1 (14.6 g, 30 mmol) and compound 26-2 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 26. (12.6 g, yield 71%, MS: [M+H)) + =591).

[0606] Synthesis Example 27

[0607]

[0608] Compound 26-1 (14.6 g, 30 mmol) and compound 27-2 (16.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 27. (13.8 g, yield 69%, MS: [M+H]) + =667).

[0609] Synthesis example 28

[0610]

[0611] Compound 26-1 (14.6 g, 30 mmol) and compound 28-2 (15.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 28. (14.5 g, yield 65%, MS: [M+H]) + =743).

[0612] Synthesis Example 29

[0613]

[0614] Compound 26-1 (14.6 g, 30 mmol) and compound 29-2 (12.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 29. (14.0 g, yield 70%, MS: [M+H)) + =667).

[0615] Example 1

[0616] ITO (indium tin oxide) is used as 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.

[0617] On the ITO transparent electrode prepared in this way, the following compound [HI-A] is applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. On this hole injection layer, hexanitrile hexaazabenzophenanthrene (HAT) with the following chemical formula is sequentially vacuum-deposited. And the following compound [HT-A] This forms a hole transport layer.

[0618] Next, on the aforementioned hole transport layer, with a film thickness... A light-emitting layer was formed by vacuum evaporation of the following compounds [BH] and [BD] in a weight ratio of 25:1. On the light-emitting layer, compound 1 and [LiQ] (lithium quinolate) were vacuum evaporated in a weight ratio of 1:1, thereby achieving a light-emitting effect. 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.

[0619] 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 is such that the vacuum level is maintained at 1×10⁻⁶ during evaporation. -7 Up to 5×10 -8 This led to the creation of organic light-emitting devices.

[0620]

[0621] Example 2

[0622] In Example 1 above, compound 2 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0623] Example 3

[0624] In Example 1 above, compound 3 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0625] Example 4

[0626] In Example 1 above, compound 4 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0627] Example 5

[0628] In Example 1 above, compound 5 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0629] Example 6

[0630] In Example 1 above, compound 6 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0631] Example 7

[0632] In Example 1 above, compound 7 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0633] Example 8

[0634] In Example 1 above, compound 8 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0635] Example 9

[0636] In Example 1 above, compound 9 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0637] Example 10

[0638] In Example 1 above, compound 10 was used instead of compound 1 in the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0639] Example 11

[0640] In Example 1 above, compound 11 was used instead of compound 1 in the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0641] Example 12

[0642] In Example 1 above, compound 12 was used instead of compound 1 in the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0643] Example 13

[0644] In Example 1 above, compound 13 was used instead of compound 1 in the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0645] Example 14

[0646] In Example 1 above, compound 14 was used instead of compound 1 in the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0647] Example 15

[0648] In Example 1 above, compound 15 was used instead of compound 1 in the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0649] Example 16

[0650] In Example 1 above, compound 16 was used instead of compound 1 in the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0651] Example 17

[0652] In Example 1 above, compound 17 was used instead of compound 1 in the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0653] Example 18

[0654] In Example 1 above, compound 18 was used instead of compound 1 in the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0655] Example 19

[0656] In Example 1 above, compound 19 was used instead of compound 1 in the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0657] Example 20

[0658] In Example 1 above, compound 20 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0659] Example 21

[0660] In Example 1 above, compound 21 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0661] Example 22

[0662] In Example 1 above, compound 22 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0663] Example 23

[0664] In Example 1 above, compound 23 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0665] Example 24

[0666] In Example 1 above, compound 24 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0667] Example 25

[0668] In Example 1 above, compound 25 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0669] Example 26

[0670] In Example 1 above, compound 26 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0671] Example 27

[0672] In Example 1 above, compound 27 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0673] Example 28

[0674] In Example 1 above, compound 28 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0675] Example 29

[0676] In Example 1 above, compound 29 was used instead of compound 1 for the electron injection and transport layer. Otherwise, the organic light-emitting device was fabricated using the same method as in Example 1.

[0677] Comparative Example 1

[0678] In Example 1 above, compound ET1 was used instead of compound 1 in the electron injection and transport layer. Otherwise, an organic light-emitting device was fabricated using the same method as in Example 1.

[0679] [ET1]

[0680]

[0681] Comparative Example 2

[0682] In Example 1 above, compound ET2 was used instead of compound 1 for the electron injection and transport layer. Otherwise, an organic light-emitting device was fabricated using the same method as in Example 1.

[0683] [ET2]

[0684]

[0685] Comparative Example 3

[0686] In Example 1 above, compound ET3 was used instead of compound 1 for the electron injection and transport layer. Otherwise, an organic light-emitting device was fabricated using the same method as in Example 1.

[0687] [ET3]

[0688]

[0689] Comparative Example 4

[0690] In Example 1 above, compound ET4 was used instead of compound 1 for the electron injection and transport layer. Otherwise, an organic light-emitting device was fabricated using the same method as in Example 1.

[0691] [ET4]

[0692]

[0693] Comparative Example 5

[0694] In Example 1 above, compound ET5 was used instead of compound 1 for the electron injection and transport layer. Otherwise, an organic light-emitting device was fabricated using the same method as in Example 1.

[0695] [ET5]

[0696]

[0697] Comparative Example 6

[0698] In Example 1 above, compound ET6 was used instead of compound 1 for the electron injection and transport layer. Otherwise, an organic light-emitting device was fabricated using the same method as in Example 1.

[0699] [ET6]

[0700]

[0701] For organic light-emitting devices fabricated using the various compounds as electron injection and transport layer materials as described in Examples 1 to 29 and Comparative Examples 1 to 6 above, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time it took for the brightness to reach 98% of its initial value (LT98) was measured at a current density.

[0702] The results are shown in Table 13 below.

[0703] [Table 13]

[0704]

[0705]

[0706] As shown in Table 13 above, since the N-containing heterocyclic derivatives and cyano groups of Formula 1 have electron-depleted structures, the polarity (dipole moment) of the molecules can be increased, thus smoothly regulating the electron mobility of organic light-emitting devices containing compounds represented by Formula 1. Therefore, it can be confirmed that the driving voltage, current efficiency, and lifetime of the organic light-emitting devices of Examples 1 to 29 exhibit superior characteristics compared to the compounds of Comparative Examples 1 to 6.

[0707] Furthermore, it is known that the compound of this application containing R3 containing a six-membered ring of N has higher molecular polarity than the compound of Comparative Example 4 containing R3 containing benzimidazole (a five-membered ring of N). The resonance structure allows for relatively smooth regulation of electron migration, resulting in excellent driving voltage, current efficiency, and lifetime.

[0708] The above-mentioned chemical formula 1 is a structure of xaton (or thioxanth), cyano, and an organic combination of N-containing monocyclic heterocyclic groups. Comparative Examples 5 and 6 are organic light-emitting devices containing compounds in which spirodifluorene (fluorene) is used instead of xaton (or thioxanth). It is known that due to the organic combination of the above-mentioned chemical formula 1, Examples 1 to 29, as organic light-emitting devices of the above-mentioned chemical formula 1, have superior driving voltage, current efficiency, and lifetime compared to Comparative Examples 5 and 6.

Claims

1. A compound represented by the following chemical formula 1: Chemical Formula 1 In the chemical formula 1, X1 is O or S, any one to three of Y1 to Y5 are N, and the rest are each independently CR3. R1 and R2 may be the same or different from each other, and are each independently phenyl, naphthyl, pyridyl, dibenzofuranyl or dibenzothiopheneyl. R3 is hydrogen. The phenyl group may be substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a straight-chain or branched alkyl group having 1 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with a cyano group; naphthyl; phenanthrene; fluoranyl; pyridyl; dibenzofuranyl; or dibenzothiopheneyl, or optionally combined with adjacent groups to form a benzene ring. L1 is directly bonded, phenylene, naphthylene, biphenylene, divalent pyridyl, divalent dibenzofuranyl, or divalent dibenzothiopheneyl. l1 is 1, m is 1, and n is 1.

2. The compound according to claim 1, wherein, The chemical formula 1 is represented by the following chemical formula 2 or 3: Chemical formula 2 Chemical formula 3 In chemical formulas 2 and 3, R1, R2, Y1 to Y5, L1, l1, m, and n are defined in the same way as in chemical formula 1.

3. The compound according to claim 1, wherein, The chemical formula 1 is represented by the following chemical formula 4 or 5: Chemical formula 4 Chemical formula 5 In chemical formulas 4 and 5, X1, R1, R2, Y1 to Y5, L1 and l1 are defined in the same way as in chemical formula 1.

4. The compound according to claim 1, wherein, The chemical formula 1 is represented by any one of the following chemical formulas 6 to 9: Chemical Formula 6 Chemical Formula 7 Chemical Formula 8 Chemical formula 9 In chemical formulas 6 to 9, R1, R2, Y1 to Y5, L1 and l1 are defined as in chemical formula 1.

5. The compound according to claim 1, wherein, Chemical Formula 1 is selected from any of the following compounds: Wherein, * represents the chemical formula 1.

6. 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, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, wherein, The organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, wherein the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound.

8. The organic light-emitting device according to claim 6, wherein, The organic layer includes a hole-blocking layer, which contains the compound.

9. The organic light-emitting device according to claim 6, wherein, The organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, wherein the hole injection layer, the hole transport layer, or the hole injection and transport layer contains the compound.

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