Novel compounds and organic light-emitting devices comprising the same

Abstract

The present application provides a novel compound and an organic light emitting device using the same.

Description

Technical Field

[0001] Cross-reference with related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2020-0057322 dated May 13, 2020 and Korean Patent Application No. 10-2021-0062018 dated May 13, 2021, the entire contents of which are disclosed in the documents of the Korean patent applications and are incorporated in this specification.

[0003] This invention relates to novel compounds and organic light-emitting devices containing the same. Background Technology

[0004] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) utilizing organic light emission exhibit wide viewing angles, excellent contrast ratios, fast response times, and superior brightness, driving voltage, and response speed characteristics, thus attracting extensive research.

[0005] Organic light-emitting devices (OLEDs) typically have a structure comprising an anode and a cathode, and an organic layer located between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials, such as a hole injection layer, a hole transport layer, an electron suppression layer, a light-emitting layer, a hole blocking 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, which emit light when they re-enter the ground state.

[0006] For organic materials used in organic light-emitting devices as described above, there is a continuous need to develop new materials.

[0007] Existing technical documents

[0008] Patent documents

[0009] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] This invention relates to novel compounds and organic light-emitting devices containing the same.

[0012] Solution to the problem

[0013] This invention provides compounds represented by the following chemical formula 1:

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] Y is either O or S.

[0018] R1 can be hydrogen; deuterium; halogen; cyano; or substituted or unsubstituted C. 1-60 Alkyl; substituted or unsubstituted C 1-60 Alkoxy; substituted or unsubstituted C 2-60 Alkenyl; substituted or unsubstituted C 2-60 Alkyne group; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0019] n1 is an integer from 0 to 6.

[0020] n2 is an integer from 0 to 3.

[0021] One of R2 is chemical formula 2, and the others are hydrogen or deuterium.

[0022] [Chemical Formula 2]

[0023]

[0024] In the above chemical formula 2,

[0025] L is a single bond, or C is substituted or unsubstituted. 6-60 Alpha-aryl

[0026] X is either N or CH, but at least two of X are N.

[0027] Ar1 and Ar2 are each independently substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatic compounds.

[0028] In addition, the present invention provides an organic light-emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the above chemical formula 1.

[0029] Invention Effects

[0030] The compounds represented by the above-described chemical formula 1 can be used as materials for the organic layer of organic light-emitting devices, thereby achieving improved efficiency, lower driving voltage, and / or improved lifetime characteristics in organic light-emitting devices. In particular, the compounds represented by the above-described chemical formula 1 can be used as materials for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection. Attached Figure Description

[0031] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

[0032] Figure 2 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. Detailed Implementation

[0033] The invention will now be described in more detail to aid in understanding.

[0034] In this instruction manual, This indicates a bond that is linked to other substituents.

[0035] In this specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thio group. aryl thiols alkylsulfonyl arylsulfonyl Silyl; boronyl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; arylene; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphinyl; or a substituent formed by connecting two or more of the above-exemplified substituents, either substituted or unsubstituted. For example, "a substituent formed by connecting two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent formed by connecting two phenyl groups.

[0036] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferred to have 1 to 40 carbon atoms. Specifically, it can be a group with the following structure, but is not limited thereto.

[0037]

[0038] In this specification, the oxygen atom in the ester group may be replaced by a straight-chain, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a group with the following structural formula, but is not limited thereto.

[0039]

[0040] In this specification, the number of carbon atoms in the imide group is not particularly limited, but it is preferred to have 1 to 25 carbon atoms. Specifically, it can be a group with the following structure, but is not limited thereto.

[0041]

[0042] In this specification, silanes specifically include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited to these.

[0043] In this specification, boron groups specifically include trimethylboronyl, triethylboronyl, tert-butyldimethylboronyl, triphenylboronyl, phenylboronyl, etc., but are not limited to these.

[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 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0046] 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 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. 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.

[0047] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0048] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0049] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure. When the fluorene group is substituted as described above, it can become... Etc. But it is not limited to this.

[0050] In this specification, a heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as heteroelements. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazole, and thiazolyl. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, iso Azolyl, thiadiazolyl, phenthiazinyl, and dibenzofuranyl groups, but not limited to these.

[0051] In this specification, the aryl groups in aralkyl, aryl-alkenyl, alkylaryl, and arylamine are the same as those exemplified above. In this specification, the alkyl groups in aralkyl, alkylaryl, and alkylamine are the same as those exemplified above. In this specification, the heteroaryl groups in heteroarylamines are subject to the above description of heterocyclic groups. In this specification, the alkenyl groups in aryl-alkenyl are the same as those exemplified above. In this specification, arylene is a divalent group; otherwise, the above description of aryl groups applies. In this specification, heteroarylene is a divalent group; otherwise, the above description of heterocyclic groups applies. In this specification, the hydrocarbon ring is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of aryl or cycloalkyl groups applies. In this specification, the heterocycle is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of heterocyclic groups applies.

[0052] The present invention provides compounds represented by the above chemical formula 1.

[0053] The compounds represented by the above-described chemical formula 1 can improve the characteristics of organic light-emitting devices by incorporating heterocycles containing two or more nitrogen atoms at specific positions in a core structure formed by the fusion of a fluoranthene ring with a bicyclic heterocycle containing O or S. In particular, the compounds represented by the above-described chemical formula 1, by using a polycyclic aromatic core with multiple aromatic rings connected together, increase the binding force (rigidity) of the molecule, improve the stability of electrons and holes, and exhibit better light-emitting properties, thereby improving quantum efficiency and lifetime.

[0054] In the above chemical formula 1, depending on the specific position where the heterocycle containing two or more nitrogen atoms is bonded, the compound represented by the above chemical formula 1 can be represented by the following chemical formula 1-1 or 1-2:

[0055] [Chemical Formula 1-1]

[0056]

[0057] [Chemical Formula 1-2]

[0058]

[0059] In the above chemical formulas 1-1 and 1-2,

[0060] Y, R1, n1, n2, L, X, Ar1, and Ar2 are defined in the same way as in the above chemical formula 1.

[0061] Specifically, in the above chemical formulas 1, 1-1, and 1-2, Y is O or S.

[0062] Specifically, in the above chemical formulas 1, 1-1, and 1-2, R1 can be hydrogen, deuterium, halogen, or cyano; or substituted or unsubstituted C. 1-20 Alkyl, or C 1-12 Alkyl, or C 1-6 Alkyl; or substituted or unsubstituted C 1-20 alkoxy, or C 1-12 alkoxy, or C 1-6 Alkoxy; or substituted or unsubstituted C 2-20 alkenyl, or C 2-12 alkenyl, or C 2-6 Alkenyl; or substituted or unsubstituted C 2-20 alkynyl group, or C 2-12 alkynyl group, or C 2-6 Alkyne group; or substituted or unsubstituted C 3-30 cycloalkyl, or C 3-25 cycloalkyl, or C 3-20 cycloalkyl; or substituted or unsubstituted C 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-20 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 3-30 heteroaryl, or C 5-28 heteroaryl, or C 5-25 heteroaryl, or C 6-20 heteroaryl, or C 12-18 Mixed aromatic compounds.

[0063] As an example, R1 can be either hydrogen or deuterium. Alternatively, R1 can be entirely hydrogen.

[0064] Specifically, in the above chemical formulas 1, 1-1, and 1-2, n1 and n2 can each be an integer from 0 to 2, or 0 or 1.

[0065] Specifically, in the above chemical formulas 1, 1-1, and 1-2, L can be a single bond; or a substituted or unsubstituted C. 6-30 aryl, or C 6-28 aryl, or C 6-25 aryl, or C 6-20 Aryl group. Preferably, L can be a single bond; or phenylene, biphenylene, terphenylene, tetraphenylene, or naphthylene.

[0066] As an example, L can be a single bond or can be represented by any of the groups selected from the following groups.

[0067]

[0068] Specifically, in the above chemical formula 1, chemical formula 1-1, and chemical formula 1-2, two of X can be N and the rest can be CH, or all of X can be N.

[0069] Specifically, in the aforementioned chemical formulas 1, 1-1, and 1-2, Ar1 and Ar2 can each be substituted or unsubstituted C. 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-20 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 3-30 heteroaryl, or C 5-30 heteroaryl, or C 5-28 heteroaryl, or C 5-25 heteroaryl, or C 6-20 heteroaryl, or C 12-18 Mixed aromatic compounds.

[0070] More specifically, Ar1 and Ar2 can each be phenyl, naphthyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, carbazoyl-substituted phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophene, carbazoyl, or phenyl-substituted carbazoyl.

[0071] In particular, at least one of Ar1 and Ar2 can be phenyl, naphthyl-substituted phenyl, biphenyl, naphthyl, or phenyl-substituted naphthyl.

[0072] Representative examples of compounds represented by the above chemical formula 1 are shown below.

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089] On the other hand, the compound represented by the above chemical formula 1 can be manufactured by the manufacturing method shown in reaction formula 1 or reaction formula 2 below. The above manufacturing method can be further specified in the synthesis examples described later.

[0090] [Reaction Formula 1]

[0091]

[0092] In the above reaction formula 1, Y, R1, R2, n1, and n2 are defined as in the above chemical formula 1; one of Q1 is BO2C2(CH3)4 or B(OH)2, and the rest are hydrogen or deuterium; Q2 is a halogen group, preferably Cl, Br, or I, more preferably Cl.

[0093] [Reaction 2]

[0094]

[0095] In the above reaction formula 2, Y, R1, R2, n1 and n2 are defined in the same way as in the above chemical formula 1, one of Q3 is a halogen group, preferably Cl, Br or I, more preferably Cl, the rest of Q3 are hydrogen or deuterium, and Q4 is BO2C2(CH3)4 or B(OH)2.

[0096] Specifically, reactions 1 and 2 described above involve introducing a heteroaryl substituent containing at least two N atoms at a specific position in a core structure formed by the fusion of a fluoranthene ring with a bicyclic heterocycle containing O or S. In such reactions, when the leaving group such as BO2C2(CH3)4 or B(OH)2 is combined with an intermediate compound containing a fluoranthene ring, a compound of formula 1 can be produced according to reaction 1; and when the leaving group such as BO2C2(CH3)4 or B(OH)2 is combined with an intermediate compound containing a heteroaryl substituent containing at least two N atoms, a compound of formula 1 can be produced according to reaction 2.

[0097] As an example, reaction formula 1 above is carried out as follows: a polycyclic compound consisting of a pinacolborane group (BO2C2(CH3)4) or a boronic acid group (B(OH)2) in Q1, formed by the fusion of a fluoranthene ring with a bicyclic heterocycle containing O or S, and a heterocyclic compound containing at least two N atoms in Q2, which is a halogen group, are reacted in the presence of a base using a palladium catalyst (Pd catalyst). Through this reaction, a heteroaryl group containing at least two N atoms is introduced into the Q1 position of the pinacolborane group (BO2C2(CH3)4) or B(OH)2 in the polycyclic compound consisting of a fluoranthene ring with a bicyclic heterocycle containing O or S. Preferably, in reaction formula 1 above, Q1 can be BO2C2(CH3)4 and Q2 can be chlorine. Specific reaction conditions for such reaction formula 1 can be implemented with reference to reactions known in the art. The above manufacturing method can be further specified in the synthetic examples described later.

[0098] As another example, reaction formula 2 above is carried out as follows: a polycyclic compound in which one of Q3 is a halogen group and is formed by fusion of a fluoranthene ring with a bicyclic heterocycle containing O or S, and a heterocyclic compound in which Q4 contains at least two N atoms as BO2C2(CH3)4 or a borate group, i.e., B(OH)2, are reacted in the presence of a base using a palladium catalyst. Through this reaction, a heteroaryl group containing at least two N atoms is introduced into the Q3 position, which is a halogen group, in the polycyclic compound formed by fusion of a fluoranthene ring with a bicyclic heterocycle containing O or S. Preferably, in reaction formula 2 above, Q3 can be chlorine and Q4 can be BO2C2(CH3)4. Specific reaction conditions for such reaction formula 2 can be implemented with reference to reactions known in the art. The above manufacturing method can be further specified in the synthetic examples described later.

[0099] Furthermore, in the above-mentioned reaction formulas 1 and 2, the base component can be potassium carbonate (K2CO3), sodium bicarbonate (NaHCO3), cesium carbonate (Cs2CO3), sodium acetate (NaOAc), potassium acetate (KOAc), sodium tert-butoxide (NaOtBu), sodium ethoxide (NaOEt), or triethylamine (Et3N), N,N-diisopropylethylamine (EtN(iPr)2), etc. Preferably, the above-mentioned base component can be potassium carbonate (K2CO3), cesium carbonate (Cs2CO3), potassium acetate (KOAc), sodium tert-butoxide (NaOtBu), or N,N-diisopropylethylamine (EtN(iPr)2).

[0100] In addition, in the above reaction formulas 1 and 2, the palladium catalysts mentioned above can be tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4, tris(dibenzylideneacetone)-dipalladium(0), Pd2(dba)3), bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu3)2, bis(dibenzylideneacetone)palladium(0), Pd(dba)2) or palladium(II)acetate, Pd(OAc)2, etc. Preferably, the palladium catalyst described above can be tetrakis(triphenylphosphine)palladium(O))(Pd(PPh3)4), bis(tris(tert-butylphosphine)palladium(O))(Pd(P-tBu3)2), or bis(dibenzylideneacetone)palladium(O))(Pd(dba)2. In particular, in reaction formula 1 above, tetrakis(triphenylphosphine)palladium(O))(Pd(PPh3)4) can be used as the catalyst, and in reaction formula 2 above, bis(tris(tert-butylphosphine)palladium(O))(Pd(P-tBu3)2) can be used as the catalyst.

[0101] In this specification, equivalent (eq.) refers to molar equivalent.

[0102] On the other hand, the present invention provides an organic light-emitting device comprising a compound represented by the above-described chemical formula 1. As an example, the present invention provides an organic light-emitting device comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the above-described chemical formula 1.

[0103] The organic layer of the organic light-emitting device of the present invention can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of the present invention can have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer as organic layers. However, the structure of the organic light-emitting device is not limited to this and may include fewer organic layers.

[0104] In addition, the aforementioned organic layer may include a hole injection layer, a hole transport layer, or a layer that performs both hole injection and transport simultaneously, wherein the aforementioned hole injection layer, hole transport layer, or layer that performs both hole injection and transport simultaneously comprises a compound represented by the aforementioned chemical formula 1.

[0105] In addition, the aforementioned organic layer may include an electron suppression layer comprising a compound represented by the aforementioned chemical formula 1.

[0106] In addition, the aforementioned organic layer may include a light-emitting layer, which contains a compound represented by the aforementioned chemical formula 1.

[0107] In addition, the aforementioned light-emitting layer also contains dopant compounds.

[0108] In addition, the above-mentioned light-emitting layer contains a compound of chemical formula 1 and a dopant.

[0109] As an example, the light-emitting layer described above contains a compound of chemical formula 1 and a dopant, and contains the compound of chemical formula 1 and the dopant in a content ratio of 100:1 to 1:1.

[0110] In addition, the light-emitting layer contains a compound of chemical formula 1 and a dopant, and contains the compound of chemical formula 1 and the dopant in a content ratio of 100:1 to 2:1.

[0111] In addition, the light-emitting layer contains a compound of chemical formula 1 and a dopant, and contains the compound of chemical formula 1 and the dopant in a content ratio of 100:1 to 5:1.

[0112] As an example, the dopant mentioned above is a metal complex.

[0113] Specifically, the dopant mentioned above is an iridium-based metal complex.

[0114] In addition, the organic layer mentioned above includes a light-emitting layer, which contains a dopant, and the dopant material is selected from the following structural formula.

[0115]

[0116]

[0117]

[0118]

[0119] The structures described above are dopant compounds, but are not limited to them.

[0120] In addition, the aforementioned organic layer may include a hole-blocking layer comprising a compound represented by the aforementioned chemical formula 1.

[0121] In addition, the aforementioned organic layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron injection and transport, wherein the aforementioned electron transport layer, electron injection layer, or layer that simultaneously performs electron injection and transport contains a compound represented by the aforementioned chemical formula 1.

[0122] In addition, the aforementioned organic layer includes a light-emitting layer and a hole transport layer, and the light-emitting layer or hole transport layer may contain a compound represented by the aforementioned chemical formula 1.

[0123] Furthermore, the organic light-emitting device according to the present invention can be a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. Additionally, the organic light-emitting device according to the present invention can be a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated below. Figure 1 and Figure 2 .

[0124] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 may be included in the light-emitting layer.

[0125] Figure 2The illustration shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. In the structure described above, the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, hole transport layer, electron suppression layer, light-emitting layer, hole blocking layer, and electron injection and transport layer. Specifically, the compound represented by Chemical Formula 1 may be included in the light-emitting layer or the hole transport layer; for example, it may be included therein as the host material of the light-emitting layer.

[0126] The organic light-emitting device according to the present invention, except that one or more of the organic layers contain a compound represented by the above-described chemical formula 1, can be manufactured using materials and methods known in the art. Furthermore, when the organic light-emitting device comprises a plurality of organic layers, the organic layers can be formed from the same substance or different substances.

[0127] For example, the organic light-emitting device according to the present invention 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, an electron suppression layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection 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.

[0128] Furthermore, the compound represented by the above chemical formula 1 can be used to form organic layers in the manufacture of organic light-emitting devices not only by vacuum evaporation but also by solution coating. In particular, the compound represented by the above chemical formula 1 has excellent solubility in the solvents used in solution coating, thus making it easy to apply solution coating methods. Here, solution coating methods refer to, but are not limited to, spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roll coating.

[0129] Hereinafter, the present invention provides a coating composition comprising a compound represented by the above-described chemical formula 1 and a solvent.

[0130] The solvents mentioned above are not particularly limited as long as they can dissolve or disperse the compounds according to the present invention. Examples include chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, and other chlorinated solvents; tetrahydrofuran, dichloromethane, dichlorobenzene, etc. Ether solvents such as alkanes; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, and diethoxyethane. Polyols such as methane, triethylene glycol monoethyl ether, glycerol, and 1,2-hexanediol and their derivatives; alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as butyl benzoate and methyl 2-methoxybenzoate; tetrahydronaphthalene; and 3-phenoxy-toluene. Furthermore, one of the above-mentioned solvents can be used alone or in combination with two or more solvents.

[0131] Furthermore, the viscosity of the above-described coating composition is preferably from 1 cP to 10 cP, within which it is easily coated. Additionally, the concentration of the compound according to the invention in the above-described coating composition is preferably from 0.1 wt / v% to 20 wt / v%.

[0132] Furthermore, the present invention provides a method for forming a functional layer using the above-described coating composition. Specifically, it includes: a step of coating the above-described coating composition according to the present invention by a solution process; and a step of heat-treating the coated composition.

[0133] In the above heat treatment step, the heat treatment temperature is preferably between 150°C and 230°C. Furthermore, the heat treatment time is between 1 minute and 3 hours, more preferably between 10 minutes and 1 hour. Additionally, the heat treatment is preferably performed in an atmosphere of inert gas such as argon or nitrogen.

[0134] As an example, the first electrode is the anode and the second electrode is the cathode; or the first electrode is the cathode and the second electrode is the anode.

[0135] 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. Specific examples of the aforementioned anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0136] As the cathode material described above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0137] The aforementioned hole injection layer is a layer that injects holes from the electrode. Preferably, the hole injection material is a compound that possesses the ability to transport holes, the effect of injecting holes from the anode, excellent hole injection performance for the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and exhibits excellent thin film formation capability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between that of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene.

[0138] 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 material capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; materials with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers that simultaneously contain conjugated and non-conjugated portions, but are not limited to these.

[0139] The aforementioned luminescent material is capable of emitting light in the visible light region by receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining them. Preferably, it is a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole compounds; diluted styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds including azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0140] 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 carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited thereto. Preferably, the compound according to the invention is used as the main material described above.

[0141] 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 amino groups, such as pyrene, anthracene, etc. Diindrone pyrene, etc., styrylamine compounds are compounds in which at least one aryl vinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., but they are not limited to these. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these. Preferably, iridium-based metal complexes are used as the above-mentioned dopant materials.

[0142] The aforementioned light-emitting layer can be a red light-emitting layer. When the compound according to the present invention is used as the host material, the stability of electrons and holes is increased, and the energy transfer from the host to the red dopant is well realized. At the same time, the driving voltage, luminous efficiency and lifetime characteristics of the organic light-emitting device can be improved.

[0143] The aforementioned electron transport layer receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is one capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer; materials with high electron mobility are suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, 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, examples of suitable cathode materials are common materials with low work functions and accompanied by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium are all accompanied by an aluminum or silver layer.

[0144] The aforementioned electron injection layer is a layer that injects electrons from the electrode. Preferably, it is a compound that possesses the ability to transport electrons, the effect of injecting electrons from the cathode, excellent electron injection effect for the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the hole injection layer, and has excellent thin film forming ability. Specifically, it includes fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0145] 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.

[0146] The organic light-emitting device according to the present invention can be a bottom-emission device, a top-emission device, or a bidirectional light-emitting device, and in particular, it can be a bottom-emission device that requires relatively high luminous efficiency.

[0147] In addition, the compounds according to the present invention can be included not only in organic light-emitting devices, but also in organic solar cells or organic transistors.

[0148] The manufacture of compounds represented by the above chemical formula 1 and organic light-emitting devices containing them is specifically described in the following examples. However, the following examples are for illustrative purposes only and the scope of the invention is not limited thereto.

[0149] Synthesis Example A. Synthesis of intermediate compound a

[0150]

[0151] 1) Preparation of compound a-3

[0152] Add 15.6 g (0.02 equivalent) of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), Pd(dppf)Cl2, and 313.7 g (3.00 equivalent) of potassium acetate (KOAc) to 300 g (1.0 equivalent) of 2-bromo-1-chlorodibenzo[b,d]furan, 297.7 g (1.1 equivalent) of bis(pinac olato)diboron, and 313.7 g (3.00 equivalent) of potassium acetate (KOAc) to 6000 mL of 1,4-dichlorodibenzo[b,d]furan. In a alkane (1,4-dioxnae), the mixture was refluxed and stirred. After 3 hours, the reaction was complete, and the solvent was removed under reduced pressure. The filtered solid was completely dissolved in CHCl3, washed with water, and the solution containing the product was concentrated under reduced pressure to remove approximately 90% of the solvent. Ethanol was added again under reflux to allow crystals to settle. After cooling, the mixture was filtered to give 273.1 g of compound a-3 (78% yield). [M+H] + =330.

[0153] 2) Preparation of compound a-2

[0154] 273.1 g (1.0 equivalent) of compound a-3 and 347.4 g (1.1 equivalent) of 1,8-diiodonaphthalene were added to 5462 mL of tetrahydrofuran (THF), and the mixture was stirred and refluxed. Then, 344.6 g (3.0 equivalent) of potassium carbonate (K₂CO₃) dissolved in 1034 mL of water was added, and after thorough stirring, 19.2 g (0.02 equivalent) of tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄) was added. After 5 hours, the reaction was allowed to proceed. The mixture was then cooled to room temperature, and the organic and aqueous layers were separated by distillation. The organic layer was then completely dissolved in ethyl acetate, washed with water, and subjected to reduced pressure to remove approximately 80% of the solvent. Hexane was added again under reflux to allow the crystals to settle, and the mixture was cooled and filtered. It was purified by silica gel column chromatography to obtain 238.1 g of compound a-2 (yield 63%). [M+H] + =456.

[0155] 3) Preparation of compound a-1

[0156] 238.1 g (1.0 equivalent) of compound a-2 was mixed with 2.7 g (0.01 equivalent) of bis(tri-tert-butylphosphine)palladium(0)(Pd(P-tBu3)2) and 144.7 g (2.00 equivalent) of potassium carbonate (K2CO3), and then added to 2.5 L of N,N-dimethylacetamide. The mixture was refluxed and stirred. After 3 hours, the reactants were poured into water to allow crystals to settle, and then filtered. The filtered solid was completely dissolved in 1,2-dichlorobenzene, washed with water, and the solution containing the product was concentrated under reduced pressure to allow crystals to settle. After cooling, the solution was filtered. The solution was purified by silica gel column chromatography to give 78.7 g of compound a-1 (yield 46%). [M+H] + =328.

[0157] 4) Preparation of compound a

[0158] 78.7 g (1.0 equivalent) of compound a-1 and 67.3 g (1.1 equivalent) of bis(pinacol) diborone were mixed in 1574 mL of 1,4-dioxane. The mixture was refluxed in alkane and stirred. Then, 70.9 g (3.0 equivalents) of potassium acetate (KOAc) was added, and after thorough stirring, 4.2 g (0.03 equivalents) of bis(dibenzylacetone)palladium(0) (Pd(dba)2) and 4.1 g (0.06 equivalents) of tricyclohexylphosphine (PCy3) were added. After reacting for 3 hours, the mixture was distilled under reduced pressure, dissolved again in chloroform, and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 80.6 g of compound a (80% yield). [M+H] + =419.

[0159] Synthesis Example B. Synthesis of intermediate compound b

[0160]

[0161] 1) Preparation of compound b-5

[0162] 400.0 g (1.0 equivalent) of 4-bromo-1-fluoro-2-iodobenzene and 229.1 g (1.0 equivalent) of (2-chloro-6-hydroxyphenyl)boronic acid were added to 8000 mL of tetrahydrofuran (THF) and stirred and refluxed. Then, 551.2 g (3.0 equivalent) of potassium carbonate (K₂CO₃) dissolved in 1654 mL of water was added, and after thorough stirring, 30.7 g (0.02 equivalent) of tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄) was added. After 5 hours of reaction, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled. Then, it was completely dissolved in ethyl acetate, washed with water, and then subjected to reduced pressure to remove approximately 80% of the solvent. Hexane was added again under reflux to allow the crystals to settle, and the mixture was cooled and filtered. The crystals were then purified by silica gel column chromatography to give 240.5 g of compound b-5 (60% yield). [M+H] + =303.

[0163] 2) Manufacturing of compound b-4

[0164] 240.5 g (1.0 equivalent) of compound b-5 and 330.7 g (3.0 equivalent) of potassium carbonate (K₂CO₃) were added to 2405 mL of N,N-dimethylacetamide (DMAC), refluxed, and stirred. After 4 hours, the reaction mixture was poured into water to allow crystals to settle, and then filtered. The filtered solid was completely dissolved in chloroform, washed with water, and anhydrous magnesium sulfate was added. After stirring, the mixture was filtered again, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 206.6 g of compound b-4 (92% yield). [M+H] + =283.

[0165] 3) Preparation of compound b-3

[0166] Compound b-3 was synthesized by means of the same method as that used to produce compound a-3, except that compound b-4 was used instead of 2-bromo-1-chlorodibenzo[b,d]furan.

[0167] 4) Preparation of compound b-2

[0168] Compound b-2 was synthesized by using compound b-3 instead of compound a-3, except that compound b-2 was synthesized by the same method as compound a-2 described above.

[0169] 5) Preparation of compound b-1

[0170] Compound b-1 was synthesized by using compound b-2 instead of compound a-2, except that compound b-1 was synthesized by the same method as compound a-1 described above.

[0171] 6) Manufacturing of compound b

[0172] Compound b was synthesized using the same method as that used for the preparation of compound a, except that compound b-1 was used instead of compound a-1.

[0173] Synthesis Example C. Synthesis of intermediate compound c

[0174] 1) Preparation of compound c-1

[0175] Compound c-1 was synthesized by means of the same method as compound a-1 above, except that 2-bromo-1-chlorodibenzo[b,d]thiophene was used instead of 2-bromo-1-chlorodibenzo[b,d]furan.

[0176]

[0177] 2) Preparation of compound c

[0178] Compound c was synthesized using the same method as that used for the preparation of compound a, except that compound c-1 was used instead of compound a-1.

[0179]

[0180] Synthesis Example D. Synthesis of intermediate compound d

[0181]

[0182] 1) Preparation of compound d-6

[0183] 300.0 g (1.0 equivalent) of (4-bromo-2-iodophenyl)(methyl)sulfane and 142.6 g (1.0 equivalent) of (2-chlorophenyl)boronic acid were added to 6000 mL of tetrahydrofuran (THF), and the mixture was stirred and refluxed. Then, 378.1 g (3.0 equivalent) of potassium carbonate (K₂CO₃) dissolved in 1134 mL of water was added, and after thorough stirring, 21.1 g (0.02 equivalent) of tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄) was added. After 2 hours, the reaction was allowed to proceed. The mixture was then cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then completely dissolved in ethyl acetate, washed with water, and the solvent was removed again under reduced pressure (approximately 80% of the solvent was removed). Hexane was added again under reflux to allow the crystals to settle, and the mixture was cooled and filtered. The compound was purified by silica gel column chromatography to yield 214.5 g of compound d-6 (75% yield). [M+H] + =315.

[0184] 2) Manufacturing of compound d-5

[0185] 46.5 g (2.00 equivalents) of H₂O₂ was added to 214.5 g (1.0 equivalent) of compound d-6, and then added to 1 L of acetic acid (AcOH). The mixture was refluxed and stirred. After 1 hour, the reaction mixture was poured into water to allow crystals to settle, and then filtered. The filtered solid was completely dissolved in ethyl acetate, washed with water, and then subjected to reduced pressure to remove approximately 80% of the solvent. Hexane was added again under reflux to allow crystals to settle, and the mixture was cooled and filtered. The mixture was purified by silica gel column chromatography to give 81.2 g of compound d-5 (yield 36%). [M+H] + =331.

[0186] 3) Manufacturing of compound d-4

[0187] 81.2 g (1.0 equivalent) of compound d-5 and 450 mL of H₂SO₄ were added, and the mixture was refluxed while stirring to dissolve. After 2 hours, when the reaction was complete, the reactants were poured into water to allow crystals to settle, and then filtered. The filtered solid was completely dissolved in CHCl₃, washed with water, and the solution containing the product was concentrated under reduced pressure to remove approximately 80% of the solvent. Hexane was added again under reflux to allow crystals to settle, and after cooling, the mixture was filtered to obtain 27.9 g of compound d-4 (yield 38%). [M+H] + =299.

[0188] 4) Preparation of compound d-3

[0189] Compound d-3 was synthesized by the same method as that used to produce compound a-3, except that compound d-4 was used instead of 2-bromo-1-chlorodibenzo[b,d]furan.

[0190] 5) Preparation of compound d-2

[0191] Compound d-2 was synthesized by using compound d-3 instead of compound a-3, except that compound d-2 was synthesized by the same method as compound a-2 described above.

[0192] 6) Preparation of compound d-1

[0193] Compound d-2 was used instead of compound a-2, and compound d-1 was synthesized by the same method as that used to produce compound a-1.

[0194] 7) Manufacturing of compound d

[0195] Compound d was synthesized by using compound d-1 instead of compound a-1, except that compound d was synthesized by the same method as compound a described above.

[0196] Synthesis Example 1. Synthesis of Compound 1

[0197]

[0198] Compound sub1 (15 g, 38.1 mmol) and compound a (17.5 g, 41.9 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.3 g of compound 1. (Yield 70%, MS: [M+H)) + =651).

[0199] Synthesis Example 2. Synthesis of Compound 2

[0200]

[0201] Compound 2 (15 g, 40.1 mmol) and compound a (18.5 g, 44.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (16.6 g, 120.4 mmol) was dissolved in 50 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.2 g of compound 2. (Yield 60%, MS: [M+H)) + =631).

[0202] Synthesis Example 3. Synthesis of Compound 3

[0203]

[0204] Compound 3 (15 g, 42 mmol) and compound a (19.3 g, 46.2 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (17.4 g, 126.1 mmol) was dissolved in 52 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.8 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.6 g of compound 3. (Yield 80%, MS: [M+H)) + =614).

[0205] Synthesis Example 4. Synthesis of Compound 4

[0206]

[0207] Compound 4 (15 g, 38.1 mmol) and compound a (17.5 g, 41.9 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.1 g of compound 4. (Yield 69%, MS: [M+H)) + =651)

[0208] Synthesis Example 5. Synthesis of Compound 5

[0209]

[0210] Compound 5 (15 g, 40.8 mmol) and compound a (18.8 g, 44.9 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (16.9 g, 122.3 mmol) was dissolved in 51 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.3 g of compound 5. (Yield 80%, MS: [M+H)) + =625)

[0211] Synthesis Example 6. Synthesis of Compound 6

[0212]

[0213] Compound 6 (15 g, 30.9 mmol) and compound a-1 (10.1 g, 30.9 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (12.8 g, 92.7 mmol) was dissolved in 38 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.9 g of compound 6. (Yield 69%, MS: [M+H)) + =651).

[0214] Synthesis Example 7. Synthesis of Compound 7

[0215]

[0216] Compound 7 (15 g, 47.2 mmol) and compound b (21.7 g, 51.9 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (19.6 g, 141.6 mmol) was dissolved in 59 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.7 g of compound 7. (Yield 80%, MS: [M+H)) + =575).

[0217] Synthesis Example 8. Synthesis of Compound 8

[0218]

[0219] Compound 8 (15 g, 41.9 mmol) and compound b (19.3 g, 46.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.8 mmol) was added. After reacting for 9 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.5 g of compound 8. (Yield 72%, MS: [M+H)) + =615).

[0220] Synthesis Example 9. Synthesis of Compound 9

[0221]

[0222] Compound 9 (15 g, 38.1 mmol) and compound b (17.5 g, 41.9 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.6 g of compound 9. (Yield 67%, MS: [M+H)) + =651).

[0223] Synthesis Example 10. Synthesis of Compound 10

[0224]

[0225] Compound 10 (15 g, 34.6 mmol) and compound b (15.9 g, 38.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (14.4 g, 103.9 mmol) was dissolved in 43 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16 g of compound 10. (Yield 67%, MS: [M+H)) + =690).

[0226] Synthesis Example 11. Synthesis of Compound 11

[0227]

[0228] Compound 11 (15 g, 26.1 mmol) and b-1 (8.5 g, 26.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (10.8 g, 78.2 mmol) was dissolved in 32 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.1 g of compound 11. (Yield 73%, MS: [M+H)) + =741).

[0229] Synthesis Example 12. Synthesis of Compound 12

[0230]

[0231] Compound 12 (15 g, 34.5 mmol) and compound b-1 (11.3 g, 34.5 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (14.3 g, 103.4 mmol) was dissolved in 43 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.8 g of compound 12. (Yield 62%, MS: [M+H)) + =601).

[0232] Synthesis Example 13. Synthesis of Compound 13

[0233]

[0234] Compound 13 (15 g, 56 mmol) and compound c (26.8 g, 61.6 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in 70 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(O) (1.3 g, 1.1 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23 g of compound 13. (Yield 76%, MS: [M+H)) + =541).

[0235] Synthesis Example 14. Synthesis of Compound 14

[0236]

[0237] Compound 14 (15 g, 35.9 mmol) and compound c (17.1 g, 39.5 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (14.9 g, 107.7 mmol) was dissolved in 45 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.3 g of compound 14. (Yield 74%, MS: [M+H)) + =691).

[0238] Synthesis Example 15. Synthesis of Compound 15

[0239]

[0240] Compound 15 (15 g, 35.7 mmol) and compound c (17.1 g, 39.3 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (14.8 g, 107.2 mmol) was dissolved in 44 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After reacting for 9 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.8 g of compound 15. (Yield 76%, MS: [M+H)) + =693).

[0241] Synthesis Example 16. Synthesis of Compound 16

[0242]

[0243] Compound 16 (15 g, 40.1 mmol) and compound c (19.2 g, 44.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (16.6 g, 120.4 mmol) was dissolved in 50 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.3 g of compound 16. (Yield 63%, MS: [M+H)) + =647).

[0244] Synthesis Example 17. Synthesis of Compound 17

[0245]

[0246] Compound 17 (15 g, 30.9 mmol) and compound c-1 (10.6 g, 30.9 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (12.8 g, 92.7 mmol) was dissolved in 38 mL of water and added to the solution. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.3 g of compound 17. (Yield 60%, MS: [M+H)) + =667).

[0247] Synthesis Example 18. Synthesis of Compound 18

[0248]

[0249] Compound 18 (15 g, 43.6 mmol) and compound d (20.8 g, 48 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (18.1 g, 130.9 mmol) was dissolved in 54 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.3 g of compound 18. (Yield 68%, MS: [M+H)) + =617).

[0250] Synthesis Example 19. Synthesis of Compound 19

[0251]

[0252] Compound 19 (15 g, 41.9 mmol) and compound d (20 g, 46.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (1 g, 0.8 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.9 g of compound 19. (Yield 64%, MS: [M+H)) + =631).

[0253] Synthesis Example 20. Synthesis of Compound 20

[0254]

[0255] Compound 20 (15 g, 35.7 mmol) and compound d (17.1 g, 39.3 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (14.8 g, 107.2 mmol) was dissolved in 44 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.8 g of compound 20. (Yield 76%, MS: [M+H)) + =693).

[0256] Synthesis Example 21. Synthesis of Compound 21

[0257]

[0258] Compound 21 (15 g, 28 mmol) and compound d-1 (9.6 g, 28 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (11.6 g, 84 mmol) was dissolved in 35 mL of water and added, stirred thoroughly, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol). After reacting for 11 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then redissolved in chloroform, washed twice with water, and the organic layer was separated again. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.6 g of compound 21. (Yield 78%, MS: [M+H)) + =717).

[0259] Synthesis Example 22. Synthesis of Compound 22

[0260]

[0261] Compound 22 (15 g, 34.6 mmol) and compound d (16.6 g, 38.1 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (14.4 g, 103.9 mmol) was dissolved in 43 mL of water and added to the solution. After thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.8 g, 0.7 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.9 g of compound 22. (Yield 61%, MS: [M+H)) + =706).

[0262] Example 1

[0263] ITO (indium tin oxide) was applied at 1000 angstroms ( A glass substrate coated with an ITO film of a thickness of [insert thickness here] was immersed in distilled water containing detergent and ultrasonically washed. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing with 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.

[0264] On the prepared ITO transparent electrode, as a hole injection layer, the following compound HI-1 is applied... A hole-injection layer is formed by thermal vacuum evaporation of a material to a thickness of [thickness value missing], and compound A-1 is p-doped at a concentration of 1.5%. Compound HT-1 is then vacuum-deposited onto the hole-injection layer to form a film of [thickness value missing]. The hole transport layer. Next, on the aforementioned hole transport layer, at a film thickness of... An electron suppression layer was formed by vacuum evaporation of compound EB-1. Then, compound 1 and compound Dp-7 were vacuum evaporated onto the EB-1 film at a weight ratio of 98:2 to form... A red luminescent layer of a certain thickness. On the aforementioned luminescent layer, a film thickness of... A hole-blocking layer was formed by vacuum evaporation of the following compound HB-1. Next, compounds ET-1 and LiQ were vacuum evaporated onto the hole-blocking layer in a 2:1 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.

[0265]

[0266] 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 was such that the vacuum level was maintained at 2×10⁻⁶ during evaporation. -7 Up to 5×10 -6 This led to the creation of organic light-emitting devices.

[0267] Examples 2 to 22

[0268] In the organic light-emitting device of Example 1, compounds 2 to 22 as described in Table 1 below were used instead of compound 1, and the organic light-emitting device was otherwise manufactured by the same method as in Example 1 above.

[0269]

[0270] Comparative Examples 1 to 8

[0271] In the organic light-emitting device of Example 1, compound 1 was replaced by the compounds listed in Table 1 below. Otherwise, the organic light-emitting device was manufactured by the same method as in Example 1 above. The compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, and C-8 used in Table 1 below are shown below.

[0272]

[0273] When a current was applied to the organic light-emitting devices manufactured in the above embodiments and comparative examples, the voltage and efficiency (15 mA / cm²) were measured. 2 The results are shown in Table 1 below. Lifetime T95 refers to the time required for the brightness to decrease from the initial brightness (6000 nits) to 95%.

[0274] [Table 1]

[0275] distinguish substance Drive voltage (V) Efficiency (cd / A) Lifespan T95 (hr) Luminous color Example 1 Compound 1 3.71 18.8 135 red Example 2 Compound 2 3.79 17.3 107 red Example 3 Compound 3 3.78 17.0 114 red Example 4 Compound 4 3.73 18.2 122 red Example 5 Compound 5 3.68 18.7 105 red Example 6 Compound 6 3.74 18.3 121 red Example 7 Compound 7 3.68 19.0 134 red Example 8 Compound 8 3.63 19.6 156 red Example 9 Compound 9 3.65 19.3 123 red Example 10 Compound 10 3.72 18.5 118 red Example 11 Compound 11 3.70 18.2 106 red Example 12 Compound 12 3.61 19.9 142 red Example 13 Compound 13 3.82 17.3 125 red Example 14 Compound 14 3.78 17.8 131 red Example 15 Compound 15 3.76 18.0 117 red Example 16 Compound 16 3.85 17.3 105 red Example 17 Compound 17 3.89 17.0 103 red Example 18 Compound 18 3.72 18.7 126 red Example 19 Compound 19 3.80 17.8 101 red Example 20 Compound 20 3.68 18.5 109 red Example 21 Compound 21 4.76 17.7 106 red Example 22 Compound 22 3.71 18.3 122 red Comparative Example 1 C-1 4.20 14.9 84 red Comparative Example 2 C-2 4.25 13.6 72 red Comparative Example 3 C-3 4.01 15.3 79 red Comparative Example 4 C-4 4.51 8.9 13 red Comparative Example 5 C-5 4.59 7.8 10 red Comparative Example 6 C-6 4.06 15.1 62 red Comparative Example 7 C-7 3.97 16.4 93 red Comparative Example 8 C-8 4.05 15.3 81 red

[0276] When an electric current was applied to the organic light-emitting devices fabricated according to Examples 1 to 22 and Comparative Examples 1 to 8, the results shown in Table 1 were obtained. The red organic light-emitting device of Example 1, as described above, used a material widely used in the past, and had a structure in which compound EB-1 was used as an electron suppression layer, and compound 1 and compound Dp-7 were used as red light-emitting layers. Furthermore, in Comparative Examples 1 to 8, organic light-emitting devices were fabricated using compounds C-1 to C-8 instead of compound 1.

[0277] As shown in Table 1 above, according to the present invention, the organic light-emitting devices of Examples 1 to 22, which use compounds represented by Chemical Formula 1 (i.e., compounds with specific polycyclic structures containing two or more N-containing heteroaryl substituents at specific positions in a core structure formed by the fusion of a fluoranthene ring and a bicyclic heterocycle containing O or S) as the light-emitting layer, exhibit significantly lower driving voltages and significantly higher efficiency compared to the organic light-emitting devices of Comparative Examples 1 to 8 manufactured using the compounds of C-1, C-2, C-3, C-4, C-5, C-6, C-7, and C-8 described above. This indicates that energy transfer from the host to the red dopant is well achieved. Furthermore, it is evident that the organic light-emitting devices of Examples 1 to 22 can significantly improve lifetime characteristics while maintaining high efficiency. This can ultimately be attributed to the higher stability of electrons and holes of the compounds according to the embodiments of the present invention compared to the compounds of the comparative examples. In conclusion, it can be confirmed that using the compounds of the present invention as the host of the red light-emitting layer can improve the driving voltage, luminous efficiency, and lifetime characteristics of organic light-emitting devices.

[0278] [Symbol Explanation]

[0279] 1: Substrate 2: Anode

[0280] 3: Light-emitting layer 4: Cathode

[0281] 5: Hole injection layer; 6: Hole transport layer

[0282] 7: Electron suppression layer; 8: Hole blocking layer

[0283] 9: Electron injection and transport layer.

Claims

1. A compound represented by the following chemical formula 1: Chemical Formula 1 In the chemical formula 1, Y is either O or S. R1 is independently hydrogen; or deuterium. n1 is an integer from 0 to 6. n2 is an integer from 0 to 3. One of R2 is chemical formula 2, and the others are hydrogen or deuterium. Chemical formula 2 In the chemical formula 2, L can be a single bond, a phenylene group, or a naphthylene group. X is always N, Ar1 and Ar2 are each independently phenyl, naphthyl-substituted phenyl, carbazolyl-substituted phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or phenyl-substituted carbazolyl.

2. The compound according to claim 1, wherein, Compounds represented by chemical formula 1 are represented by chemical formula 1-1 or 1-2. Chemical Formula 1-1 Chemical formula 1-2 In the chemical formulas 1-1 and 1-2, Y, R1, n1, n2, L, X, Ar1, and Ar2 are the same as defined in claim 1.

3. The compound according to claim 1, wherein, L stands for a single bond.

4. The compound according to claim 1, wherein, L is a single bond, or is represented by any of the groups selected from the following:

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

6. An organic light-emitting device, wherein, include: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, wherein, The organic layer containing the compound is a light-emitting layer.

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