Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device comprising the same.

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2023-0015599, filed with the Korean Patent Office on February 6, 2023, the entire contents of which are contained in this specification.

[0002] This specification relates to compounds and organic light-emitting devices containing them. Background Technology

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

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

[0005] Technical issues

[0006] This specification provides compounds and organic light-emitting devices containing them.

[0007] Solution to the problem

[0008] One embodiment of this specification provides a compound of the following chemical formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] At least one of Y1 to Y5 is N, and the remaining Y1 to Y5 that are not N are either the same as or different from each other, and are each independently CR4.

[0013] At least one of Y6 to Y10 is N, and the remaining Y6 to Y10 that are not N are either the same as or different from each other, and are each independently CR5.

[0014] R1 to R3 may be the same as or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0015] R4 and R5 may be the same as or different from each other, and each may independently be hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or any pair or more adjacent groups may be combined to form a substituted or unsubstituted ring.

[0016] Z1 is a cyano group.

[0017] At least one of L1 and L2 is directly bonded, and the other is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0018] l1 and l2 are each integers from 1 to 3.

[0019] When there are 2 or more L1 values, the 2 or more L1 values ​​are either the same or different from each other.

[0020] When there are 2 or more L2s, the two or more L2s mentioned above are either the same or different from each other.

[0021] In addition, one embodiment of this specification provides an organic light-emitting device, including: a first electrode, a second 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.

[0022] Invention Effects

[0023] The compounds described in this specification can be used as materials for the organic layer of organic light-emitting devices. The compounds according to at least one embodiment of this specification can achieve improved efficiency, lower driving voltage, and / or improved lifetime characteristics in organic light-emitting devices. Attached Figure Description

[0024] Figure 1 and 2 An example of an organic light-emitting device according to one embodiment of this specification is illustrated.

[0025] [Symbol Explanation]

[0026] 1: Substrate

[0027] 2: First electrode

[0028] 3: Second electrode

[0029] 4: Organic layer

[0030] 5: Hole injection layer

[0031] 6: First Hole Transport Layer

[0032] 7: Second Hole Transport Layer

[0033] 8: Emissive layer

[0034] 9: Electron Injection and Transport Layer Detailed Implementation

[0035] This specification provides for compounds of the above chemical formula 1.

[0036] According to one embodiment of this specification, the above-described chemical formula 1 is a compound having Z1 centrally bonded to benzene, and a six-membered monocyclic or polycyclic heteroaryl group containing one or more nitrogen atoms bonded at positions 2 and 3, or positions 2 and 6, via linking groups L1 or L2. By having an electron-depleted structure such as a six-membered monocyclic or polycyclic heteroaryl group containing one or more nitrogen atoms, the polarity (dipole moment) of the molecule in chemical formula 1 can be increased. Therefore, by including chemical formula 1 in the organic layer of an organic light-emitting device, improved efficiency, lower driving voltage, and improved lifetime characteristics can be achieved.

[0037] According to one embodiment of this specification, Z1 of the above-described chemical formula 1 is a cyano group, thus increasing the polarity (dipole moment value) of the molecule, increasing the stability of the organic light-emitting device containing it, and having the effects of improved efficiency and lifetime, as well as reduced voltage. Furthermore, at least one of L1 and L2 of the above-described chemical formula 1 is directly bonded, thus improving the stability of the molecule, thereby demonstrating the effect of improved lifetime of the organic light-emitting device.

[0038] Throughout this specification, the term "combination of them" in the Markush form of the expression refers to a mixture or combination of one or more of the constituent elements described in the Markush form of the expression, indicating that it includes one or more of the constituent elements mentioned above.

[0039] Examples of substituents in this specification are described below, but are not limited thereto.

[0040] In this instruction manual, Indicates the part that is connected.

[0041] 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.

[0042] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, cyano, alkyl, cycloalkyl, alkoxy, alkenyl, haloalkyl, silyl, boron, amino, aryl, fused ring groups of aromatic and aliphatic hydrocarbon rings, and heteroaryl, or substituted by two or more substituents linked together as exemplified above, or without any substituents.

[0043] In this specification, "two or more substituents linked" means that the hydrogen of any one substituent is linked to another substituent. For example, two substituents linked can be a phenyl group linked to a naphthyl group to 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 above definition also applies to connections of four or more substituents.

[0044] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0045] 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, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0046] In this specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl with 3 to 30 carbon atoms. Specifically, it includes 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 is not limited to these.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] In this specification, aryl is not particularly limited, but is preferably an aryl with 6 to 30 carbon atoms, and the aryl can be monocyclic or polycyclic.

[0051] 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.

[0052] 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.

[0053] In this specification, the fluorene group can be substituted, and adjacent groups can combine with each other to form a ring.

[0054] When the aforementioned fluorene group is replaced, there is

[0055]

[0056] etc., but not limited to this.

[0057] 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.

[0058] 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 heteroaryl 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 (p henoxathiine), phen Phenoxazine, phenothiazine, dihydroindocarbazolyl, spirofluorenylxanthinyl, and spirofluorenylthioxanthinyl are examples, but not limited to these.

[0059] 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.

[0060] In this specification, the boron group can be -BR 100 R 101 The above R 100 and R 101Whether identical or different, each group can independently be selected from hydrogen, deuterium, halogen, nitrile, substituted or unsubstituted monocyclic or polycyclic cycloalkyl groups with 3 to 30 carbon atoms, substituted or unsubstituted straight-chain or branched alkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups with 2 to 30 carbon atoms. Specific examples of the aforementioned boryl groups include dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, etc., but are not limited to these.

[0061] 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, 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] In this specification, the hydrocarbon cyclic group can be an aromatic hydrocarbon cyclic group, an aliphatic hydrocarbon cyclic group, or a fused cyclic group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring. The aromatic hydrocarbon cyclic group is subject to the above description of aryl groups, and the aliphatic hydrocarbon cyclic group is subject to the above description of cycloalkyl groups. Furthermore, the fused cyclic group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring is subject to the above-described structure of fused aryl and cycloalkyl groups.

[0068] 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.

[0069] 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.

[0070] In one embodiment of this specification, the portion of chemical formula 1 without substituents may refer to the portion substituted with hydrogen or deuterium.

[0071] In this specification, the meaning of "adjacent groups combine with each other to form a ring" in the context of substituents refers to the combination with adjacent groups to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, and 1,4-dioxane. Alkane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxacycloheptane, azirrocyclooctane, thiocyclooctane, etc., but not limited to these.

[0076] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. Methods and materials similar to or equivalent to those described herein may be used to implement or test embodiments of the invention, but suitable methods and materials are described later. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, unless a specific passage is mentioned, this specification, including its definitions, takes precedence. Furthermore, materials, methods, and embodiments are illustrative only and not intended to be limiting.

[0077] The compounds of the above chemical formula 1 will now be described in detail.

[0078] According to one embodiment of this specification, the portion of chemical formula 1 above that is not bound with substituents indicates that it is bound with hydrogen.

[0079] According to one embodiment of this specification, the above-mentioned chemical formula 1 is chemical formula 1-1 or chemical formula 1-2.

[0080] [Chemical Formula 1-1]

[0081]

[0082] [Chemical Formula 1-2]

[0083]

[0084] In the above chemical formulas 1-1 and 1-2,

[0085] The definitions of Y1 to Y10, L1, L2, l1, l2, Z1 and R1 to R3 are the same as those in Chemical Formula 1 above.

[0086] According to one embodiment of this specification, R1 to R3 are hydrogen.

[0087] According to one embodiment of this specification, l1 is 1.

[0088] According to one embodiment of this specification, l1 is 2.

[0089] According to one embodiment of this specification, l1 is 3.

[0090] According to one embodiment of this specification, l2 is 1.

[0091] According to one embodiment of this specification, l2 is 2.

[0092] According to one embodiment of this specification, l2 is 3.

[0093] In this specification, when l1 is 2 or more in the above chemical formula 1, two or more L1s may be the same or different from each other, and each L1 indicates that they are connected in series. For example, when l1 is 3, and each L1 is phenylene, naphthylene, and phenylene, they can be connected as shown below, but are not limited thereto, and the order or connection position of each L1 may be different.

[0094]

[0095] In addition, the above For example, when l1 is 3, it indicates that it is bonded to the terminal substituent at the third position in the structure illustrated above, i.e., the phenylene group. * indicates the site of bonding with chemical formula 1 above. It is the part that connects to the end of L1 mentioned above.

[0096] The explanation of l1 above also applies to the explanation of l2.

[0097] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0098] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder is a substituted or unsubstituted aryl group.

[0099] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder is a monocyclic or polycyclic arylene with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 30 substituted or unsubstituted carbon atoms.

[0100] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder is a monocyclic or polycyclic arylene with 6 to 20 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 20 substituted or unsubstituted carbon atoms.

[0101] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0102] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder is a monocyclic or polycyclic arylene group with 6 to 20 carbon atoms, either substituted or unsubstituted.

[0103] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder is arylene or heteroarylene.

[0104] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder is a monocyclic or polycyclic arylene with 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 30 carbon atoms.

[0105] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder is a monocyclic or polycyclic arylene with 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 20 carbon atoms.

[0106] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder are monocyclic or polycyclic arylene groups with 6 to 30 carbon atoms.

[0107] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder are monocyclic or polycyclic arylene groups with 6 to 20 carbon atoms.

[0108] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder is phenylene or divalent pyridyl.

[0109] According to one embodiment of this specification, at least one of L1 and L2 is directly bonded, and the remainder is phenylene.

[0110] According to one embodiment of this specification, L1 and L2 are directly bonded.

[0111] According to one embodiment of this specification, L1 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and L2 is a direct bond.

[0112] According to one embodiment of this specification, L1 is a substituted or unsubstituted aryl group, and L2 is a direct bond.

[0113] According to one embodiment of this specification, L1 is a monocyclic or polycyclic arylene with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 30 substituted or unsubstituted carbon atoms, and L2 is a direct bond.

[0114] According to one embodiment of this specification, L1 is a monocyclic or polycyclic arylene with 6 to 20 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 20 substituted or unsubstituted carbon atoms, and L2 is a direct bond.

[0115] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, and L2 is a direct bond.

[0116] According to one embodiment of this specification, L1 is a monocyclic or polycyclic arylene group with 6 to 20 substituted or unsubstituted carbon atoms, and L2 is a direct bond.

[0117] According to one embodiment of this specification, L1 is arylene or heteroarylene, and L2 is direct bonding.

[0118] According to one embodiment of this specification, L1 is a monocyclic or polycyclic arylene with 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 30 carbon atoms, and L2 is a direct bond.

[0119] According to one embodiment of this specification, L1 is a monocyclic or polycyclic arylene with 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 20 carbon atoms, and L2 is a direct bond.

[0120] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, and L2 is a direct bond.

[0121] According to one embodiment of this specification, L1 is a monocyclic or polycyclic aryl group with 6 to 20 carbon atoms, and L2 is a direct bond.

[0122] According to one embodiment of this specification, L1 is a phenylene group or a divalent pyridinyl group, and L2 is a direct bond.

[0123] According to one embodiment of this specification, L1 is a phenylene oxide and L2 is a direct bond.

[0124] According to one embodiment of this specification, L2 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and L1 is a direct bond.

[0125] According to one embodiment of this specification, L2 is a substituted or unsubstituted aryl group, and L1 is a direct bond.

[0126] According to one embodiment of this specification, L2 is a monocyclic or polycyclic arylene with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 30 substituted or unsubstituted carbon atoms, and L1 is a direct bond.

[0127] According to one embodiment of this specification, L2 is a monocyclic or polycyclic arylene with 6 to 20 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 20 substituted or unsubstituted carbon atoms, and L1 is a direct bond.

[0128] According to one embodiment of this specification, L2 is a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, and L1 is a direct bond.

[0129] According to one embodiment of this specification, L2 is a monocyclic or polycyclic arylene group with 6 to 20 substituted or unsubstituted carbon atoms, and L1 is a direct bond.

[0130] According to one embodiment of this specification, L2 is an arylene or heteroarylene, and L1 is a direct bond.

[0131] According to one embodiment of this specification, L2 is a monocyclic or polycyclic arylene with 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 30 carbon atoms, and L1 is a direct bond.

[0132] According to one embodiment of this specification, L2 is a monocyclic or polycyclic arylene with 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 20 carbon atoms, and L1 is a direct bond.

[0133] According to one embodiment of this specification, L2 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, and L1 is a direct bond.

[0134] According to one embodiment of this specification, L2 is a monocyclic or polycyclic arylene group with 6 to 20 carbon atoms, and L1 is a direct bond.

[0135] According to one embodiment of this specification, L2 is a phenylene group or a divalent pyridyl group, and L1 is a direct bond.

[0136] According to one embodiment of this specification, L2 is a phenylene oxide and L1 is a direct bond.

[0137] According to one embodiment of this specification, at least one of Y1 to Y5 is N, and the remaining ones of Y1 to Y5 that are not N are the same as or different from each other, and each is independently CR4.

[0138] According to one embodiment of this specification, any one of Y1 to Y5 is N, and the remaining ones of Y1 to Y5 that are not N are the same or different from each other, and each is independently CR4.

[0139] According to one embodiment of this specification, any two of Y1 to Y5 are N, and the remaining ones of Y1 to Y5 that are not N are the same or different from each other, and each is independently CR4.

[0140] According to one embodiment of this specification, any three of Y1 to Y5 are N, and the remaining ones of Y1 to Y5 that are not N are the same or different from each other, and each is independently CR4.

[0141] According to one embodiment of this specification, any four of Y1 to Y5 are N, and the remaining ones of Y1 to Y5 that are not N are CR4.

[0142] According to one embodiment of this specification, Y1 to Y5 are N.

[0143] According to one embodiment of this specification, Y1 is N, and Y2 to Y5 are the same as or different from each other, each being CR4 independently.

[0144] According to one embodiment of this specification, Y2 is N, and Y1 and Y3 to Y5 are the same or different from each other, and each is independently CR4.

[0145] 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 CR4.

[0146] According to one embodiment of this specification, Y1 and Y2 are N, and Y3 to Y5 are the same as or different from each other, each being CR4 independently.

[0147] According to one embodiment of this specification, Y1 and Y3 are N, and Y2, Y4 and Y5 are the same as or different from each other, each being CR4 independently.

[0148] According to one embodiment of this specification, Y1 and Y4 are N, and Y2, Y3 and Y5 are the same as or different from each other, each being CR4 independently.

[0149] According to one embodiment of this specification, Y1 and Y5 are N, and Y2 to Y4 are the same as or different from each other, each being CR4 independently.

[0150] According to one embodiment of this specification, Y2 and Y3 are N, and Y1, Y4 and Y5 are the same as or different from each other, each being CR4 independently.

[0151] According to one embodiment of this specification, Y2 and Y4 are N, and Y1, Y3 and Y5 are the same as or different from each other, each being CR4 independently.

[0152] According to one embodiment of this specification, Y1, Y2 and Y3 are N, and Y4 and Y5 are the same as or different from each other, each being CR4 independently.

[0153] According to one embodiment of this specification, Y1, Y2 and Y4 are N, Y3 and Y5 are the same as or different from each other, and each is independently CR4.

[0154] According to one embodiment of this specification, Y1, Y2 and Y5 are N, and Y3 and Y4 are the same as or different from each other, each being CR4 independently.

[0155] According to one embodiment of this specification, Y1, Y3 and Y4 are N, Y2 and Y5 are the same as or different from each other, and each is independently CR4.

[0156] According to one embodiment of this specification, Y1, Y3 and Y5 are N, and Y2 and Y4 are the same as or different from each other, each being CR4 independently.

[0157] According to one embodiment of this specification, Y2 to Y4 are N, Y1 and Y5 are the same as or different from each other, and each is independently CR4.

[0158] According to one embodiment of this specification, Y1 and Y3 to Y5 are N, and Y2 is CR4.

[0159] According to one embodiment of this specification, Y1, Y2, Y4 and Y5 are N, and Y3 is CR4.

[0160] According to one embodiment of this specification, Y1 to Y4 are N, and Y5 is CR4.

[0161] According to one embodiment of this specification, at least one of Y6 to Y10 is N, and the remaining Y6 to Y10 that are not N are the same as or different from each other, and each is independently CR5.

[0162] According to one embodiment of this specification, any one of Y6 to Y10 is N, and the remaining ones of Y6 to Y10 that are not N are the same or different from each other, and each is independently CR5.

[0163] According to one embodiment of this specification, any two of Y6 to Y10 are N, and the remaining Y6 to Y10 that are not N are the same or different from each other, and each is independently CR5.

[0164] According to one embodiment of this specification, any three of Y6 to Y10 are N, and the remaining ones of Y6 to Y10 that are not N are the same or different from each other, and each is independently CR5.

[0165] According to one embodiment of this specification, any four of Y6 to Y10 are N, and the remaining ones of Y6 to Y10 that are not N are CR5.

[0166] According to one embodiment of this specification, Y6 to Y10 are N.

[0167] According to one embodiment of this specification, Y6 is N, and Y7 to Y10 may be the same as or different from each other, each being CR5 independently.

[0168] According to one embodiment of this specification, Y7 is N, and Y6 and Y8 to Y10 are the same as or different from each other, and each is independently CR5.

[0169] According to one embodiment of this specification, Y8 is N, and Y6, Y7, Y9 and Y10 are the same as or different from each other, and each is independently CR5.

[0170] According to one embodiment of this specification, Y6 and Y7 are N, and Y8 to Y10 are the same as or different from each other, each being CR5 independently.

[0171] According to one embodiment of this specification, Y6 and Y8 are N, and Y7, Y9 and Y10 are the same as or different from each other, and each is independently CR5.

[0172] According to one embodiment of this specification, Y6 and Y9 are N, and Y7, Y8 and Y10 are the same as or different from each other, and each is independently CR5.

[0173] According to one embodiment of this specification, Y6 and Y10 are N, and Y7 to Y9 are the same as or different from each other, each being CR5 independently.

[0174] According to one embodiment of this specification, Y7 and Y8 are N, and Y6, Y9 and Y10 are the same as or different from each other, and each is independently CR5.

[0175] According to one embodiment of this specification, Y7 and Y9 are N, and Y6, Y8 and Y10 are the same as or different from each other, and each is independently CR5.

[0176] According to one embodiment of this specification, Y6, Y7 and Y8 are N, Y9 and Y10 are the same as or different from each other, and each is independently CR5.

[0177] According to one embodiment of this specification, Y6, Y7 and Y9 are N, and Y8 and Y10 are the same as or different from each other, and each is independently CR5.

[0178] According to one embodiment of this specification, Y6, Y7 and Y10 are N, and Y8 and Y9 are the same as or different from each other, each being CR5 independently.

[0179] According to one embodiment of this specification, Y6, Y8 and Y9 are N, Y7 and Y10 are the same as or different from each other, and each is independently CR5.

[0180] According to one embodiment of this specification, Y6, Y8 and Y10 are N, Y7 and Y9 are the same as or different from each other, and each is independently CR5.

[0181] According to one embodiment of this specification, Y7 to Y9 are N, Y6 and Y10 are the same as or different from each other, and each is independently CR5.

[0182] According to one embodiment of this specification, Y6 and Y8 to Y10 are N, and Y7 is CR5.

[0183] According to one embodiment of this specification, Y6, Y7, Y9 and Y10 are N, and Y8 is CR5.

[0184] According to one embodiment of this specification, Y6 to Y9 are N, and Y10 is CR5.

[0185] According to one embodiment of this specification, the above... It is selected from any of the following structures.

[0186]

[0187] In the above structure,

[0188] L1 and l1 are defined in the above chemical formula 1.

[0189] R41 to R45 may be the same as or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or any pair or more adjacent groups combined to form a substituted or unsubstituted ring.

[0190] According to one embodiment of this specification, the above... It is selected from any of the following structures.

[0191]

[0192] In the above structure,

[0193] L2 and l2 are defined in the above chemical formula 1.

[0194] R51 to R55 may be the same as or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or any pair or more adjacent groups combined to form a substituted or unsubstituted ring.

[0195] According to one embodiment of this specification, R4 is hydrogen, or a substituted or unsubstituted aryl group, or any pair or more adjacent groups combined to form a substituted or unsubstituted ring.

[0196] According to one embodiment of this specification, R4 is hydrogen, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or any pair or more adjacent groups combined to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0197] According to one embodiment of this specification, R4 is hydrogen, or a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or any pair or more adjacent groups combined to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0198] According to one embodiment of this specification, R4 is hydrogen or aryl, or any pair or more adjacent groups are combined with each other to form an aromatic hydrocarbon ring.

[0199] According to one embodiment of this specification, R4 is hydrogen, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or an aromatic hydrocarbon ring having 6 to 30 carbon atoms formed by the combination of any one or more adjacent groups.

[0200] According to one embodiment of this specification, R4 is hydrogen, or an aryl group of 6 to 20 carbon atoms in a monocyclic or polycyclic form, or an aromatic hydrocarbon ring of 6 to 20 carbon atoms formed by the combination of any pair or more adjacent groups.

[0201] According to one embodiment of this specification, R4 is hydrogen, phenyl, biphenyl, or naphthyl, or any pair or more adjacent groups combined with each other to form benzene.

[0202] According to one embodiment of this specification, R5 is hydrogen, or a substituted or unsubstituted aryl group, or any pair or more adjacent groups combined to form a substituted or unsubstituted ring.

[0203] According to one embodiment of this specification, R5 is hydrogen, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or any pair or more adjacent groups combined to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0204] According to one embodiment of this specification, R5 is hydrogen, or a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or any pair or more adjacent groups combined with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0205] According to one embodiment of this specification, R5 is hydrogen or aryl, or any pair or more adjacent groups are combined with each other to form an aromatic hydrocarbon ring.

[0206] According to one embodiment of this specification, R5 is hydrogen, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or an aromatic hydrocarbon ring having 6 to 30 carbon atoms formed by the combination of any one or more adjacent groups.

[0207] According to one embodiment of this specification, R5 is hydrogen, or an aryl group with 6 to 20 carbon atoms in a monocyclic or polycyclic form, or an aromatic hydrocarbon ring with 6 to 20 carbon atoms formed by the combination of any one or more adjacent groups.

[0208] According to one embodiment of this specification, R5 is hydrogen, phenyl, biphenyl, or naphthyl, or any pair or more adjacent groups combined with each other to form benzene.

[0209] According to one embodiment of this specification, R41 to R45 may be the same as or different from each other, each being independently hydrogen, or a substituted or unsubstituted aryl group, or any pair or more adjacent groups may be combined with each other to form a substituted or unsubstituted ring.

[0210] According to one embodiment of this specification, R41 to R45 may be the same as or different from each other, each being independently hydrogen, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or any pair or more adjacent groups are combined with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0211] According to one embodiment of this specification, R41 to R45 may be the same as or different from each other, each being independently hydrogen, or a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or any pair or more adjacent groups are combined with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0212] According to one embodiment of this specification, R41 to R45 may be the same as or different from each other, each being independently hydrogen or aryl, or any pair or more adjacent groups may be combined with each other to form an aromatic hydrocarbon ring.

[0213] According to one embodiment of this specification, R41 to R45 may be the same as or different from each other, each being independently hydrogen, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or any pair or more adjacent groups combined with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0214] According to one embodiment of this specification, R41 to R45 may be the same as or different from each other, each being independently hydrogen, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or any pair or more adjacent groups combined to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

[0215] According to one embodiment of this specification, R41 to R45 may be the same as or different from each other, each being independently hydrogen, phenyl, biphenyl or naphthyl, or any pair or more adjacent groups may be combined with each other to form benzene.

[0216] According to one embodiment of this specification, R51 to R55 may be the same as or different from each other, each being independently hydrogen, or a substituted or unsubstituted aryl group, or any pair or more adjacent groups may be combined with each other to form a substituted or unsubstituted ring.

[0217] According to one embodiment of this specification, R51 to R55 may be the same as or different from each other, each being independently hydrogen, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or any pair or more adjacent groups combined with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 substituted or unsubstituted carbon atoms.

[0218] According to one embodiment of this specification, R51 to R55 may be the same as or different from each other, each being independently hydrogen, or a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or any pair or more adjacent groups combined with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 20 substituted or unsubstituted carbon atoms.

[0219] According to one embodiment of this specification, R51 to R55 may be the same as or different from each other, each being independently hydrogen or aryl, or any pair or more adjacent groups may be combined with each other to form an aromatic hydrocarbon ring.

[0220] According to one embodiment of this specification, R51 to R55 may be the same as or different from each other, each being independently hydrogen, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or any pair or more adjacent groups combined with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0221] According to one embodiment of this specification, R51 to R55 may be the same as or different from each other, each being independently hydrogen, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or any pair or more adjacent groups combined with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

[0222] According to one embodiment of this specification, R51 to R55 may be the same as or different from each other, each being independently hydrogen, phenyl, biphenyl or naphthyl, or any pair or more adjacent groups may be combined with each other to form benzene.

[0223] According to one embodiment of this specification, the above-mentioned chemical formula 1 is selected from any of the following compounds.

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237] In addition, this specification provides organic light-emitting devices containing the compounds mentioned above.

[0238] 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.

[0239] 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.

[0240] 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.

[0241] 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.

[0242] In this specification, the meaning of a specific substance A being contained in layer C or layer D is all of the following: i) substance A is contained in one or more layers of layer C, or ii) substance A is contained in one or more layers of layer D, or iii) substance A is contained in one or more layers of layer C and one or more layers of layer D respectively.

[0243] This specification provides an organic light-emitting device, comprising: a first electrode, a second 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 of the aforementioned chemical formula 1.

[0244] 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.

[0245] 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.

[0246] According to one embodiment of this specification, the organic layer includes a hole-blocking layer, and the hole-blocking layer contains the aforementioned compound.

[0247] 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.

[0248] According to one embodiment of this specification, the organic layer includes a light-emitting layer.

[0249] According to one embodiment of this specification, the organic layer includes an electron blocking layer.

[0250] According to one embodiment of this specification, the aforementioned organic layer further includes one or more of the following: a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

[0251] 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.

[0252] 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.

[0253] 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.

[0254] 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.

[0255] According to one embodiment of this specification, the first electrode is an anode or a cathode.

[0256] According to one embodiment of this specification, the second electrode is a cathode or an anode.

[0257] 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).

[0258] 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.

[0259] For example, the structure of an organic light-emitting device according to one embodiment of this specification is illustrated in... Figure 1 and 2 The above. Figure 1 and 2 Organic light-emitting devices are illustrated, but not limited to them.

[0260] Figure 1 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The aforementioned compound is contained within the organic layer.

[0261] Figure 2 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, a light-emitting layer 8, an electron injection and transport layer 9, and a second electrode 3 are sequentially stacked on a substrate 1. The aforementioned compound is contained within the electron injection and transport layer 9.

[0262] The organic light-emitting devices described in this specification, except that the hole injection layer, electron injection layer, electron transport layer, electron injection and transport layer, or hole blocking layer contains the aforementioned compound, i.e., the compound of chemical formula 1, can be manufactured using materials and methods known in the art.

[0263] When the aforementioned organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0264] 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.

[0265] Furthermore, the compounds of Formula 1 mentioned above can be used to form organic layers not only by vacuum evaporation but also by solution coating when manufacturing organic light-emitting devices. 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.

[0266] 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.

[0267] 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.

[0268] 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.

[0269] 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.

[0270] 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.

[0271] [Chemical formula H-1]

[0272]

[0273] In the above chemical formula H-1,

[0274] 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.

[0275] 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.

[0276] 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.

[0277] 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.

[0278] 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.

[0279] 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 dibenzothiopheneyl.

[0280] 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.

[0281] 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.

[0282] 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 terphenyl 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 deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a terphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. A monocyclic or polycyclic aryl-substituted or unsubstituted phenanthryl group; a thiophene group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0283] 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.

[0284] In one embodiment of this specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0285] According to one embodiment of this specification, R201 is hydrogen.

[0286] According to one embodiment of this specification, the above chemical formula H-1 is represented by any of the following compounds, but is not limited thereto.

[0287]

[0288] 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. Examples include diindene pyrene. 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, examples include styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but these are not limited to these. Additionally, as metal complexes, examples include iridium complexes and platinum complexes, but these are not limited to these.

[0289] 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.

[0290] [Chemical Formula D-1]

[0291]

[0292] In the above chemical formula D-1,

[0293] 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 alkylsilyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0294] t5 and t6 are each integers from 1 to 4.

[0295] When t5 is 2 or more, the two or more T5 values ​​are the same or different from each other.

[0296] When t6 is 2 or more, the two or more T6 are the same or different from each other.

[0297] According to one embodiment of this specification, T1 to T6 may be the same as or different from each other, and each independently comprises hydrogen, a straight-chain or branched alkyl group having 1 to 30 substituted or unsubstituted carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 substituted or unsubstituted carbon atoms.

[0298] 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 straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, cyano, 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.

[0299] 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, tert-butyl, trimethylsilyl, unsubstituted phenyl, deuterated substituted phenyl, cyano-substituted phenyl, or methyl-substituted phenyl.

[0300] According to one embodiment of this specification, the above chemical formula D-1 is represented by any of the following compounds, but is not limited thereto.

[0301]

[0302] 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.

[0303] 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.

[0304] [Chemical formula HI-1]

[0305]

[0306] In the above chemical formula HI-1,

[0307] R301 to R306 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 heterocyclic.

[0308] L301 and L302 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.

[0309] According to one embodiment of this specification, R301 and R302 may be the same as or different from each other, and each is independently a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0310] According to one embodiment of this specification, R301 and R302 are methyl groups.

[0311] According to one embodiment of this specification, L301 and L302 are directly bonded.

[0312] According to one embodiment of this specification, R303 to R306 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 heterocyclic group.

[0313] According to one embodiment of this specification, R303 to R306 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 heterocyclic group with 2 to 30 carbon atoms substituted or unsubstituted by a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms.

[0314] According to one embodiment of this specification, R303 to R306 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.

[0315] According to one embodiment of this specification, the above-mentioned chemical formula HI-1 is represented by the following compounds, but is not limited thereto.

[0316]

[0317] 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.

[0318] 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.

[0319] [Chemical formula HT-1]

[0320]

[0321] In the above chemical formula HT-1,

[0322] At least one of X'1 to X'6 is N, and the rest are CH.

[0323] 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.

[0324] According to one embodiment of this specification, X'1 to X'6 are N.

[0325] According to one embodiment of this specification, R309 to R314 are cyano groups.

[0326] According to one embodiment of this specification, the above-mentioned chemical formula HT-1 is represented by the following compound.

[0327]

[0328] 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.

[0329] [Chemical formula HT-2]

[0330]

[0331] In the above chemical formula HT-2,

[0332] 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.

[0333] 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.

[0334] 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.

[0335] 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.

[0336] According to one embodiment of this specification, R317 is selected from carbazolyl, phenyl, biphenyl, and combinations thereof.

[0337] 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.

[0338] 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.

[0339] According to one embodiment of this specification, the above-mentioned chemical formula HT-2 is represented by the following compound.

[0340]

[0341] 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 electron transport layer other than the electron transport layer containing 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.

[0342] 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 electron injection layer other than the electron injection layer comprising the aforementioned chemical formula 1, the preferred electron injection material is one that exhibits excellent electron transport capabilities, effectively receives electrons from the second electrode, and provides excellent electron injection for the light-emitting layer or light-emitting material. Furthermore, a material that prevents excitons generated in the light-emitting layer from migrating to the hole injection layer and exhibits excellent thin-film formation capabilities is preferred. Specifically, fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc., are preferred. 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.

[0343] 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.

[0344] According to one embodiment of this specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. When the electron injection and transport layer includes an electron injection and transport layer other than the electron injection and transport layer comprising the electron injection and transport layer of the above chemical formula 1, the substances exemplified in the electron transport layer and the electron injection layer may be used, but are not limited thereto.

[0345] According to one embodiment of this specification, the electron injection and transport layer may further comprise a metal coordination compound. The metal coordination compound is as described above.

[0346] The electron blocking layer described above 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. Known materials can be used without limitation, including but not limited to the substances exemplified in the description of the hole injection layer. The electron blocking layer can be formed between the light-emitting layer and the hole transport layer, 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.

[0347] The aforementioned hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed using the same conditions as the electron injection layer. When an organic light-emitting device according to one embodiment of this specification includes a hole-blocking layer other than the hole-blocking layer comprising the aforementioned chemical formula 1, specifically, it has… Diazole or triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, etc., but not limited to these.

[0348] 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.

[0349] 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., and are not limited thereto.

[0350] Methods of implementing the invention

[0351] 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.

[0352] Manufacturing Example 1.

[0353]

[0354] Compound 1-1 (5.7 g, 30 mmol) and compound 2-chloro-4,6-diphenyl-1,3,5-triazine (17.7 g, 66 mmol) were added to tetrahydrofuran (300 mL). 2M K₂CO₃ (200 mL) and tetra(triphenylphosphine)palladium(0) (0.3 g) 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.

[0355] (13.6g, 80% yield, MS: [M+H]) + =566).

[0356] Manufacturing Example 2.

[0357]

[0358] The starting materials were used as described in the above reaction formula, except that the above compound 2 was manufactured by the same method as that used in manufacturing example 1.

[0359] MS:[M+H] + =565

[0360] Manufacturing Example 3.

[0361]

[0362] The above-mentioned compound (2-chloro-6-cyanophenyl)boronic acid (5.7 g, 30 mmol) and the above-mentioned compound 2-chloro-4,6-diphenyl-1,3,5-triazine (8.83 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K₂CO₃ (200 mL) and tetrakis(triphenylphosphine)palladium(O) (0.3 g) 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 the above-mentioned compound 3-1.

[0363] Compound 3-1 (11.06 g, 30 mmol) and compound 3-2 (16.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand (ligan d) 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.

[0364] (15.5g, yield 72%, MS: [M+H]) + =718).

[0365] Manufacturing Example 4.

[0366]

[0367] The starting materials were used as described in the above reaction formula, except that the above compound 4 was manufactured by the same method as that used in manufacturing example 1.

[0368] MS:[M+H] + =718

[0369] Manufacturing Example 5.

[0370]

[0371] The starting materials were used as described in the above reaction formula, except that the above compound 5 was manufactured by the same method as that used in manufacturing example 1.

[0372] MS:[M+H] + =718

[0373] Manufacturing Example 6.

[0374]

[0375] The starting materials were used as described in the above reaction formula, except that the above compound 6 was manufactured by the same method as that used in manufacturing example 1.

[0376] MS:[M+H] + =718

[0377] Manufacturing Example 7.

[0378]

[0379] The starting materials were used as described in the above reaction formula, except that the above compound 7 was manufactured by the same method as that used in manufacturing example 1.

[0380] MS:[M+H] + =692

[0381] Manufacturing Example 8.

[0382]

[0383] The starting materials were used as described in the above reaction formula, except that the above compound 8 was manufactured by the same method as that used in manufacturing example 1.

[0384] MS:[M+H] + =641

[0385] Manufacturing Example 9.

[0386]

[0387] The starting materials were used as described in the above reaction formula, except that the above compound 9 was manufactured by the same method as that used in manufacturing example 1.

[0388] MS:[M+H] + =717

[0389] Manufacturing Example 10.

[0390]

[0391] The starting materials were used as described in the above reaction formula, except that the above compound 10 was manufactured by the same method as that used in manufacturing example 1.

[0392] MS:[M+H] + =641

[0393] [Example]

[0394] Example 1-1

[0395] ITO (indium tin oxide) is used in... 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.

[0396] 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 the aforementioned hole injection layer, [the following is likely a separate, unrelated sentence:] ... The following compounds HAT and The following compound HT-A is sequentially vacuum-deposited to form a first hole transport layer and a second hole transport layer.

[0397] Next, on the aforementioned second hole transport layer, with a film thickness... A light-emitting layer was formed by vacuum evaporation of the following compounds BH and BD at a weight ratio of 25:1.

[0398] On the aforementioned light-emitting layer, the previously manufactured compound 1 and the following compound LiQ were vacuum-deposited in a 1:1 weight ratio, thereby achieving... The thickness forms an electron injection and transport layer. On this electron injection and transport layer, lithium fluoride (LiF) is sequentially applied... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness.

[0399]

[0400] During the above process, the evaporation rate of organic matter is maintained. to 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 -5 This led to the creation of organic light-emitting devices.

[0401] Examples 1-2 to Examples 1-10

[0402] Organic light-emitting devices were manufactured by the same method as in Examples 1-1, except that compounds 2 to 10 listed in Table 1 below were used instead of compound 1 in Examples 1-1.

[0403] Comparative Examples 1-1 to 1-11

[0404] Organic light-emitting devices were manufactured by replacing compound 1 in Examples 1-1 with compounds ET-1 to ET-11 listed in Table 1 below, except that the method was the same as that used in Examples 1-1. The structures of compounds ET-1 to ET-11 in Table 1 below are shown below.

[0405]

[0406] [Experimental Example]

[0407] For the organic light-emitting devices manufactured in Examples 1-1 to 1-10 and Comparative Examples 1-1 to 1-11 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 (T90) at the given current density was measured relative to the initial brightness to reach 90%. The results are shown in Table 1 below.

[0408] [Table 1]

[0409]

[0410] As described in Table 1 above, the compounds of Formula 1 according to this specification can be used in the electron injection and transport layers of organic light-emitting devices.

[0411] According to one embodiment of this specification, Chemical Formula 1 is a compound having Z1 centrally bonded to benzene, and a six-membered monocyclic or polycyclic heteroaryl group containing one or more nitrogen atoms bonded at positions 2 and 3, or positions 2 and 6, via linking groups L1 or L2. By having an electron-depleted structure such as a six-membered monocyclic or polycyclic heteroaryl group containing one or more nitrogen atoms, the polarity (dipole moment) of the molecule in Chemical Formula 1 can be increased. Therefore, by incorporating Chemical Formula 1 into the organic layer of an organic light-emitting device, improved efficiency, lower driving voltage, and improved lifetime characteristics can be achieved.

[0412] According to one embodiment of this specification, when Z1 of the above-described chemical formula 1 is a cyano group, the polarity (dipole moment value) of the molecule increases, thus increasing the stability of the organic light-emitting device containing it, resulting in improved efficiency and lifetime, and reduced voltage. Furthermore, at least one of L1 and L2 of the above-described chemical formula 1 is directly bonded, thus improving molecular stability and exhibiting an improved lifetime effect for the organic light-emitting device.

[0413] Specifically, it is known that the organic light-emitting device containing Chemical Formula 1 of this specification has superior driving voltage, efficiency, and lifetime compared to Comparative Examples 1-1, 1-4, and 1-8, which contain compounds with N-containing heteroaryl groups bonded at positions 2 and 4 of benzene; Comparative Examples 1-3, which contain compounds with N-containing heteroaryl groups bonded at positions 3 and 4 of benzene; Comparative Examples 1-5, which contain compounds with N-containing heteroaryl groups bonded at positions 2 and 5 of benzene; and Comparative Examples 1-6 and 1-7, which contain compounds with N-containing heteroaryl groups bonded at positions 3 and 5 of benzene.

[0414] Furthermore, it is known that the organic light-emitting device containing chemical formula 1 of this specification has a longer conjugation length compared to Comparative Examples 1-2, which contain compounds containing hydrogen as the substituent at the Z1 position of this specification, resulting in superior driving voltage, efficiency, and lifetime.

[0415] It is understood that the organic light-emitting device containing Chemical Formula 1 of this specification has higher molecular stability and better driving voltage, efficiency and lifetime because at least one of L1 and L2 contains direct bonding, compared with Comparative Examples 1-9, which contain compounds containing N-heteroaryl groups at positions 3 and 4 of benzene and L1 and L2 are arylene groups; and Comparative Examples 1-11, which contain N-heteroaryl groups at positions 3 and 5 of benzene and L1 and L2 are arylene groups.

[0416] The preferred embodiments of the present invention (electron injection and transport layer) have been described above, but the present invention is not limited thereto. Various modifications can be made within the scope of the claims and detailed description of the invention, and these modifications also fall within the scope of the present invention.

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, At least one of Y1 to Y5 is N, and the rest of Y1 to Y5 that are not N are the same as or different from each other and are independently CR4, At least one of Y6 to Y10 is N, and the rest of Y6 to Y10 that are not N are the same as or different from each other and are each independently CR5, R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, R4 and R5 are the same or different from each other and are independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or any one or more adjacent groups are combined to form a substituted or unsubstituted ring, Z1 is cyano, At least one of L1 and L2 is a direct bond, and the others are substituted or unsubstituted arylene groups, or substituted or unsubstituted heteroarylene groups, l1 and l2 are each an integer from 1 to 3, When the number of L1 is 2 or more, the two or more L1 are the same or different from each other. When the number of L2 is 2 or more, the two or more L2s may be the same as or different from each other.

2. The compound according to claim 1, wherein The chemical formula 1 is the following chemical formula 1-1 or 1-2: [Chemical formula 1-1] [Chemical formula 1-2] In the chemical formulas 1-1 and 1-2, Definitions of Y1 to Y10, L1, L2, l1, l2, Z1, and R1 to R3 are the same as those in Chemical Formula 1.

3. The compound according to claim 1, wherein The L1 and L2 are directly bonded.

4. The compound according to claim 1, wherein At least one of L1 and L2 is a direct bond, and the others are substituted or unsubstituted arylene groups.

5. The compound according to claim 1, wherein Said is any one selected from the following structures: In the structure, L1 and l1 are the same as those defined in the chemical formula 1, R41 to R45 are the same as or different from each other, and are independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or any one or more adjacent groups are combined to form a substituted or unsubstituted ring.

6. The compound according to claim 1, wherein Said is any one selected from the following structures: In the structure, L2 and l2 are the same as those defined in the chemical formula 1, R51 to R55 are the same as or different from each other, and are independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or any one or more adjacent groups are combined to form a substituted or unsubstituted ring.

7. The compound according to claim 1, wherein The chemical formula 1 is any one selected from the following compounds:

8. An organic light-emitting device, comprising: A first electrode, a second electrode, and one or more organic layers provided 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 7.

9. The organic light emitting device according to claim 8, wherein: The organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound.

10. The organic light emitting device according to claim 8, wherein: The organic layer includes a hole blocking layer, and the hole blocking layer includes the compound.

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