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. 10-2020-0057324 dated May 13, 2020 and Korean Patent Application No. 10-2021-0062165 dated May 13, 2021, the entire contents of which are disclosed in the documents of the Korean patent applications and are incorporated herein by reference.

[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] Each Y bond can be an independent single bond, or an O or S bond, but at least one Y bond must be an O or S bond.

[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; substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S 2-60 Mixed aromatics,

[0019] n1 and n2 are integers from 0 to 4.

[0020] n3 is an integer from 0 to 3.

[0021] R2 is represented by the following chemical formula 2.

[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; 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, or 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 ( ); Arylthio ( ); alkylsulfonyl ( ); arylsulfonyl ( ); silyl; boronyl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; arylene; alkylaryl; alkylamine; aralkylamine; heteroarylamine; arylamine; arylphosphinyl; or a substituent formed by connecting two or more of the above-exemplified substituents, either substituted or unsubstituted, containing one or more of the N, O, and S atoms. 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 any one of the following chemical formulas 1-1 to 1-8:

[0055] [Chemical Formula 1-1]

[0056]

[0057] [Chemical Formula 1-2]

[0058]

[0059] [Chemical Formulas 1-3]

[0060]

[0061] [Chemical Formulas 1-4]

[0062]

[0063] [Chemical Formulas 1-5]

[0064]

[0065] [Chemical Formulas 1-6]

[0066]

[0067] [Chemical Formulas 1-7]

[0068]

[0069] [Chemical Formulas 1-8]

[0070]

[0071] In the above chemical formulas 1-1 to 1-8,

[0072] Z is either O or S.

[0073] R1, n1, n2, n3, L, X, Ar1, and Ar2 are defined in the same way as in the above chemical formula 1.

[0074] Specifically, in the above chemical formula 1, one of Y is O or S, and the rest are single bonds.

[0075] Specifically, in the above chemical formulas 1 and 1-1 to 1-8, 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 2-6Alkyne 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.

[0076] As an example, R1 can be either hydrogen or deuterium. Alternatively, R1 can be entirely hydrogen.

[0077] Specifically, in the above chemical formula 1 and chemical formulas 1-1 to 1-8, n1, n2 and n3 can each be an integer from 0 to 2, or 0 or 1.

[0078] Specifically, in the above chemical formulas 1 and 1-1 to 1-8, 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.

[0079] As an example, L can be a single bond or can be represented by any of the groups selected from the following groups.

[0080]

[0081] Specifically, in the above chemical formula 1 and chemical formulas 1-1 to 1-8, two of X can be N and the rest can be CH, or all of X can be N.

[0082] Specifically, in the above chemical formulas 1 and 1-1 to 1-8, 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 5-25heteroaryl, or C 6-20 heteroaryl, or C 12-18 Mixed aromatic compounds.

[0083] More specifically, Ar1 and Ar2 can each be phenyl, naphthyl-substituted phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, or phenyl-substituted carbazoyl.

[0084] In particular, at least one of Ar1 and Ar2 can be phenyl, naphthyl-substituted phenyl, biphenyl, naphthyl, or phenyl-substituted naphthyl, preferably phenyl, biphenyl, or naphthyl.

[0085] Representative examples of compounds represented by the above chemical formula 1 are shown below.

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096] 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 below. The above manufacturing method can be further specified in the synthesis examples described later.

[0097] [Reaction Formula 1]

[0098]

[0099] In the above reaction formula 1, Y, R1, R2, n1 and n2 are defined as in the above chemical formula 1, Q1 is BO2C2(CH3)4 or B(OH)2, Q2 is a halogen group, preferably Cl, Br or I, more preferably Cl.

[0100] Specifically, the above-mentioned reaction formula 1 is a reaction in which a heteroaryl substituent containing at least two N is introduced at a specific position in a core structure formed by the fusion of a fluoranthene ring with a bicyclic heterocycle containing O or S.

[0101] 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) fused with a fluoranthene ring and a bicyclic heterocycle containing O or S, and a heterocyclic compound containing at least two N atoms (Q2) as 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 and 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.

[0102] Alternatively, the aforementioned alkali 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 aforementioned alkali component can be potassium carbonate (K2CO3), cesium carbonate (Cs2CO3), potassium acetate (KOAc), sodium tert-butoxide (NaOtBu), or N,N-diisopropylethylamine (EtN(iPr)2).

[0103] In addition, as the palladium catalysts mentioned above, bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu3)2, tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4, tris(dibenzylideneacetone)-dipalladium(0), Pd2(dba)3), bis(dibenzylideneacetone)palladium(0), Pd(dba)2, or palladium(II)acetate, Pd(OAc)2, etc., can be used. Preferably, the palladium catalyst described above can be bis(tris(tert-butyl)phosphine)palladium(O))(Pd(P-tBu3)2), tetra(triphenylphosphine)palladium(O))(Pd(PPh3)4, or bis(dibenzylacetone)palladium(O))(Pd(dba)2). In particular, in reaction formula 1 above, bis(tris(tert-butyl)phosphine)palladium(O))(Pd(P-tBu3)2) can be used as the catalyst.

[0104] In this specification, equivalent (eq.) refers to molar equivalent.

[0105] 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.

[0106] 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.

[0107] 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.

[0108] In addition, the aforementioned organic layer may include an electron suppression layer comprising a compound represented by the aforementioned chemical formula 1.

[0109] In addition, the aforementioned organic layer may include a light-emitting layer, which contains a compound represented by the aforementioned chemical formula 1.

[0110] In addition, the aforementioned light-emitting layer also contains dopant compounds.

[0111] In addition, the above-mentioned light-emitting layer contains a compound of chemical formula 1 and a dopant.

[0112] In addition, the above-mentioned light-emitting layer contains a compound of chemical formula 1 and a dopant.

[0113] 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.

[0114] 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.

[0115] 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.

[0116] As an example, the dopant mentioned above is a metal complex.

[0117] Specifically, the dopant mentioned above is an iridium-based metal complex.

[0118] 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.

[0119]

[0120]

[0121]

[0122] In addition, the aforementioned organic layer may include a hole-blocking layer comprising a compound represented by the aforementioned chemical formula 1.

[0123] 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.

[0124] 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.

[0125] 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 .

[0126] 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.

[0127] Figure 2 The 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] Hereinafter, the present invention provides a coating composition comprising a compound represented by the above-described chemical formula 1 and a solvent.

[0132] 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.

[0133] 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%.

[0134] 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.

[0135] 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.

[0136] 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.

[0137] 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.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] 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.

[0142] 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. (e.g., pyrimidine derivatives, etc., but not limited thereto. Preferably, the compound according to the invention is used as the main material described above.)

[0143] 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. Styrene compounds, such as diindronepyrene, are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted aryl amine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, styrene, styrenediamine, styrenetriamine, and styrenetetraamine are examples, but not limited to these. Furthermore, iridium complexes and platinum complexes are examples of metal complexes, but not limited to these. Preferably, iridium-based metal complexes are used as the dopant material described above.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] Manufacturing Example 1. Manufacturing of intermediate compound AA

[0152]

[0153] Under a nitrogen atmosphere, sub-compound A (20 g, 91.6 mmol) and N-bromosuccinimide (NBS, 17.1 g, 96.2 mmol) were added to 400 mL of chloroform (CHCl3) and stirred at room temperature. After reacting for 6 hours, the mixture was washed twice with water, 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 sub-compound A-1. (Yield 75%, MS: [M+H)) + =297).

[0154] Under a nitrogen atmosphere, compound A-1 (10 g, 33.7 mmol) and compound 1 (6.5 g, 37 mmol) were added to 200 mL of tetrahydrofuran (THF), stirred, and refluxed. Then, potassium carbonate (K₂CO₃, 14 g, 101 mmol) dissolved in 42 mL of water was added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0)(Pd(P-tBu₃)₂) (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 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 7.8 g of compound AA_P1 (yield 67%, MS: [M+H)). + =347).

[0155] Under a nitrogen atmosphere, compound AA_P1 (10 g, 28.8 mmol) and potassium carbonate (12 g, 86.5 mmol) were added to 200 mL of N,N-dimethylacetamide (DMAc), and the mixture was stirred and refluxed. After reacting for 9 hours, the mixture was cooled to room temperature, and the organic solvent was distilled under reduced pressure. The mixture was redissolved 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 7 g of compound AA_P2. (Yield 74%, MS: [M+H)) + =327).

[0156] Under a nitrogen atmosphere, compound AA_P2 (15 g, 45.9 mmol) and bis(pinacolato)diboron (12.8 g, 50.5 mmol) were reacted in 300 mL of 1,4-dioxane. The mixture was refluxed in 1,4-dioxane and stirred. Potassium acetate (KOAc, 6.8 g, 68.9 mmol) was then added, and after thorough stirring, bis(dibenzylacetone)palladium(0)(Pd(dba)2) (0.8 g, 1.4 mmol) and tricyclohexylphosphine (PCy3, 0.8 g, 2.8 mmol) were added. The reaction was allowed to proceed for 10 hours, cooled to room temperature, and the organic layer was separated using chloroform and water and then distilled. The organic layer was redissolved in chloroform, washed twice with water, separated again, and anhydrous magnesium sulfate was added. After stirring, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.9 g of compound AA. (Yield 67%, MS: [M+H)) + =419).

[0157] Manufacturing Example 2. Manufacturing of intermediate compound AB

[0158]

[0159] In Manufacturing Example 1 above, Compound 2 was used instead of Compound 1 as the starting material. Otherwise, 12.7 g of Compound AB was produced using the same method as in Manufacturing Example 1. (Yield 66%, MS: [M+H]) + =419).

[0160] Manufacturing Example 3. Manufacturing of intermediate compound AC

[0161]

[0162] In Manufacturing Example 1 above, Compound 3 was used instead of Compound 1 as the starting material. Otherwise, 13.2 g of Compound AC was produced using the same method as in Manufacturing Example 1. (Yield 69%, MS: [M+H]) + =419).

[0163] Manufacturing Example 4. Manufacturing of intermediate compound AD

[0164]

[0165] In Manufacturing Example 1 above, Compound 4 was used instead of Compound 1 as the starting material. Otherwise, 13.6 g of Compound AD (yield 71%, MS: [M+H]) was produced using the same method as in Manufacturing Example 1. + =419).

[0166] Manufacturing Example 5. Manufacturing of intermediate compound BA

[0167]

[0168] Under a nitrogen atmosphere, compound B (10 g, 35.6 mmol) and compound 5 (7.9 g, 39.1 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (14.7 g, 106.7 mmol) was dissolved in 44 mL of water and added, stirred thoroughly, followed by bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 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 10.1 g of compound BA_P1. (Yield 79%, MS: [M+H)) + =359).

[0169] Under a nitrogen atmosphere, compound BA_P1 (10 g, 27.9 mmol) and hydrogen peroxide (H₂O₂, 1 g, 30.7 mmol) were added to 200 mL of acetic acid (AcOH), and the mixture was stirred and refluxed. After 3 hours, the reaction mixture was poured into water to allow crystals to settle, and then filtered. The filtered solid was dissolved 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 7.6 g of compound BA_P2. (Yield 73%, MS: [M+H)) + =375).

[0170] Under a nitrogen atmosphere, compound BA_P2 (10 g, 26.7 mmol) was added to 200 mL of H2SO4 and stirred. After 2 hours, when the reaction was complete, the reactants were poured into water to allow the crystals to settle, and then filtered. The filtered solid was redissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was then distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.1 g of compound BA_P3. (Yield 67%, MS: [M+H)) + =343).

[0171] Under a nitrogen atmosphere, compound BA_P3 (15 g, 43.8 mmol) and bis(pinacol)diboron (12.2 g, 48.1 mmol) were reacted in 300 mL of 1,4-dioxanone solution. The mixture was refluxed into an alkane solution and stirred. Potassium acetate (6.4 g, 65.6 mmol) was then added, and after thorough stirring, bis(dibenzylacetone)palladium(0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.7 g, 2.6 mmol) were added. The reaction was allowed to proceed for 10 hours, cooled to room temperature, and the organic layer was separated using chloroform and water and then distilled. The organic layer was redissolved in chloroform, washed twice with water, separated again, and anhydrous magnesium sulfate was added. After stirring, the mixture was 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 BA. (Yield 80%, MS: [M+H)) + =435).

[0172] Manufacturing Example 6. Manufacturing of intermediate compound BB

[0173]

[0174] In Manufacturing Example 5 above, Compound 6 was used instead of Compound 5 as the starting material. Otherwise, 12.9 g of Compound BB was produced using the same method as in Manufacturing Example 5. (Yield 68%, MS: [M+H]) + =435).

[0175] Manufacturing Example 7. Manufacturing of intermediate compound BC

[0176]

[0177] In Manufacturing Example 5 above, Compound 7 was used instead of Compound 5 as the starting material. Otherwise, 13.9 g of Compound BC was produced using the same method as in Manufacturing Example 5. (Yield 73%, MS: [M+H]) + =435).

[0178] Manufacturing Example 8. Manufacturing of intermediate compound BD

[0179]

[0180] In Manufacturing Example 5 above, Compound 8 was used instead of Compound 5 as the starting material. Otherwise, 14.2 g of Compound BD was produced using the same method as in Manufacturing Example 5. (Yield 75%, MS: [M+H]) + =435).

[0181] Manufacturing Example 9. Manufacturing of Intermediate Compound C

[0182]

[0183] In Manufacturing Example 1 above, compound C was used instead of compound A as the starting material. Otherwise, 13.8 g of compound CA was produced using the same method as in Manufacturing Example 1. (Yield 72%, MS: [M+H]) + =419).

[0184] Manufacturing Example 10. Manufacturing of intermediate compound CB

[0185]

[0186] In Manufacturing Example 1 above, compound C was used instead of compound A as the starting material, and substance 2 was used instead of substance 1. Otherwise, 13.6 g of compound CB was manufactured using the same method as in Manufacturing Example 1. (Yield 71%, MS: [M+H]) + =419).

[0187] Manufacturing Example 11. Manufacturing of intermediate compound CC

[0188]

[0189] In Manufacturing Example 1 above, compound C was used instead of compound A as the starting material, and substance 3 was used instead of substance 1. Otherwise, 13.6 g of compound CC was produced using the same method as in Manufacturing Example 1. (Yield 71%, MS: [M+H]) + =419).

[0190] Manufacturing Example 12. Manufacturing of intermediate compound CD

[0191]

[0192] In Manufacturing Example 1 above, compound C was used instead of compound A as the starting material, and substance 4 was used instead of substance 1. Otherwise, 13.6 g of compound CD was manufactured using the same method as in Manufacturing Example 1. (Yield 71%, MS: [M+H]) + =419).

[0193] Manufacturing Example 13. Manufacturing of intermediate compound DA

[0194]

[0195] In Manufacturing Example 5 above, compound D was used instead of compound B as the starting material. Otherwise, 12.9 g of compound DA was produced using the same method as in Manufacturing Example 5. (Yield 68%, MS: [M+H]) + =435).

[0196] Manufacturing Example 14. Manufacturing of intermediate compound DB

[0197]

[0198] In Manufacturing Example 5 above, compound D was used instead of compound B as the starting material, and compound 6 was used instead of compound 5. Otherwise, 14.1 g of compound DB was produced using the same method as in Manufacturing Example 5. (Yield 74%, MS: [M+H]) + =435).

[0199] Manufacturing Example 15. Manufacturing of intermediate compound DC

[0200]

[0201] In Manufacturing Example 5 above, compound D was used instead of compound B as the starting material, and compound 7 was used instead of compound 5. Otherwise, 14.4 g of compound DC was produced using the same method as in Manufacturing Example 5. (Yield 76%, MS: [M+H]) + =435).

[0202] Manufacturing Example 16. Manufacturing of intermediate compound DD

[0203]

[0204] In Manufacturing Example 5 above, compound D was used instead of compound B as the starting material, and compound 8 was used instead of compound 5. Otherwise, 13.3 g of compound DD was manufactured using the same method as in Manufacturing Example 5. (Yield 70%, MS: [M+H]) + =435).

[0205] Synthesis Example 1. Synthesis of Compound 1

[0206]

[0207] Under a nitrogen atmosphere, compound AA (10 g, 23.9 mmol) and compound Trz1 (8.4 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.2 g of compound 1. (Yield 78%, MS: [M+H)) +=600).

[0208] Synthesis Example 2. Synthesis of Compound 2

[0209]

[0210] Under a nitrogen atmosphere, compound AA (10 g, 23.9 mmol) and compound Trz2 (9.1 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 9.8 g of compound 2. (Yield 65%, MS: [M+H)) + =630).

[0211] Synthesis Example 3. Synthesis of Compound 3

[0212]

[0213] Under a nitrogen atmosphere, compound AA (10 g, 23.9 mmol) and compound Trz3 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.6 g of compound 3. (Yield 75%, MS: [M+H)) + =650).

[0214] Synthesis Example 4. Synthesis of Compound 4

[0215]

[0216] Under a nitrogen atmosphere, compound AA (10 g, 23.9 mmol) and compound Trz4 (12.1 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 14 g of compound 4. (Yield 78%, MS: [M+H)) + =752).

[0217] Synthesis Example 5. Synthesis of Compound 5

[0218]

[0219] Under a nitrogen atmosphere, compound AB (10 g, 23.9 mmol) and compound Trz5 (7.7 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10.3 g of compound 5. (Yield 75%, MS: [M+H)) + =574).

[0220] Synthesis Example 6. Synthesis of Compound 6

[0221]

[0222] Under a nitrogen atmosphere, compound AB (10 g, 23.9 mmol) and compound Trz6 (10.2 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.9 g of compound 6. (Yield 74%, MS: [M+H)) + =676).

[0223] Synthesis Example 7. Synthesis of Compound 7

[0224]

[0225] Under a nitrogen atmosphere, compound AB (10 g, 23.9 mmol) and compound Trz7 (10.6 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.2 g of compound 7. (Yield 68%, MS: [M+H)) + =690).

[0226] Synthesis Example 8. Synthesis of Compound 8

[0227]

[0228] Under a nitrogen atmosphere, compound AC (10 g, 23.9 mmol) and compound Trz8 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.3 g of compound 8. (Yield 73%, MS: [M+H)) + =650).

[0229] Synthesis Example 9. Synthesis of Compound 9

[0230]

[0231] Under a nitrogen atmosphere, compound AC (10 g, 23.9 mmol) and compound Trz9 (8.4 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11 g of compound 9. (Yield 77%, MS: [M+H)) + =600).

[0232] Synthesis Example 10. Synthesis of Compound 10

[0233]

[0234] Under a nitrogen atmosphere, compound AC (10 g, 23.9 mmol) and compound Trz10 (11 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 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 12.3 g of compound 10. (Yield 73%, MS: [M+H)) + =706).

[0235] Synthesis Example 11. Synthesis of Compound 11

[0236]

[0237] Under a nitrogen atmosphere, compound AC (10 g, 23.9 mmol) and compound Trz11 (8.7 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.1 g of compound 11. (Yield 76%, MS: [M+H)) + =613).

[0238] Synthesis Example 12. Synthesis of Compound 12

[0239]

[0240] Under a nitrogen atmosphere, compound AD (10 g, 23.9 mmol) and compound Trz12 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 9.8 g of compound 12. (Yield 63%, MS: [M+H)) + =650).

[0241] Synthesis Example 13. Synthesis of Compound 13

[0242]

[0243] Under a nitrogen atmosphere, compound AD (10 g, 23.9 mmol) and compound Trz13 (9.1 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10.2 g of compound 13. (Yield 68%, MS: [M+H)) + =630).

[0244] Synthesis Example 14. Synthesis of Compound 14

[0245]

[0246] Under a nitrogen atmosphere, compound BA (10 g, 23 mmol) and compound Trz14 (8.4 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 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 10.3 g of compound 14. (Yield 71%, MS: [M+H)) + =630).

[0247] Synthesis Example 15. Synthesis of Compound 15

[0248]

[0249] Under a nitrogen atmosphere, compound BA (10 g, 23 mmol) and compound Trz15 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 9.2 g of compound 15. (Yield 60%, MS: [M+H)) + =666).

[0250] Synthesis Example 16. Synthesis of Compound 16

[0251]

[0252] Under a nitrogen atmosphere, compound BA (10 g, 23 mmol) and compound Trz16 (8.6 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 9.9 g of compound 16. (Yield 67%, MS: [M+H)) + =640).

[0253] Synthesis Example 17. Synthesis of Compound 17

[0254]

[0255] Under a nitrogen atmosphere, compound BA (10 g, 23 mmol) and compound Trz17 (6.3 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 9.8 g of compound 17. (Yield 79%, MS: [M+H)) + =540).

[0256] Synthesis Example 18. Synthesis of Compound 18

[0257]

[0258] Under a nitrogen atmosphere, compound BB (10 g, 23 mmol) and compound Trz18 (9.9 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.5 g of compound 18. (Yield 72%, MS: [M+H)) + =692).

[0259] Synthesis Example 19. Synthesis of Compound 19

[0260]

[0261] Under a nitrogen atmosphere, compound BB (10 g, 23 mmol) and compound Trz19 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11 g of compound 19. (Yield 72%, MS: [M+H)) + =666).

[0262] Synthesis Example 20. Synthesis of Compound 20

[0263]

[0264] Under a nitrogen atmosphere, compound BB (10 g, 23 mmol) and compound Trz20 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10.3 g of compound 20. (Yield 67%, MS: [M+H)) + =666).

[0265] Synthesis Example 21. Synthesis of Compound 21

[0266]

[0267] Under a nitrogen atmosphere, compound BC (10 g, 23 mmol) and compound Trz3 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 9.5 g of compound 21. (Yield 62%, MS: [M+H)) + =666).

[0268] Synthesis Example 22. Synthesis of Compound 22

[0269]

[0270] Under a nitrogen atmosphere, compound BC (10 g, 23 mmol) and compound Trz11 (8.4 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 9.4 g of compound 22. (Yield 65%, MS: [M+H)) + =629).

[0271] Synthesis Example 23. Synthesis of Compound 23

[0272]

[0273] Under a nitrogen atmosphere, compound BD (10 g, 23 mmol) and compound Trz12 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.6 g of compound 23. (Yield 76%, MS: [M+H)) + =666).

[0274] Synthesis Example 24. Synthesis of Compound 24

[0275]

[0276] Under a nitrogen atmosphere, compound BD (10 g, 23 mmol) and compound Trz21 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.6 g of compound 24. (Yield 76%, MS: [M+H)) + =666).

[0277] Synthesis Example 25. Synthesis of Compound 25

[0278]

[0279] Under a nitrogen atmosphere, compound BD (10 g, 23 mmol) and compound Trz22 (8.1 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 9.6 g of compound 25. (Yield 68%, MS: [M+H)) + =616).

[0280] Synthesis Example 26. Synthesis of Compound 26

[0281]

[0282] Under a nitrogen atmosphere, compound BD (10 g, 23 mmol) and compound Trz23 (10.4 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 26. (Yield 75%, MS: [M+H)) + =716).

[0283] Synthesis Example 27. Synthesis of Compound 27

[0284]

[0285] Under a nitrogen atmosphere, compound CA (10 g, 23.9 mmol) and compound Trz24 (10.8 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 13.2 g of compound 27. (Yield 79%, MS: [M+H]) + =700).

[0286] Synthesis Example 28. Synthesis of Compound 28

[0287]

[0288] Under a nitrogen atmosphere, compound CA (10 g, 23.9 mmol) and compound Trz25 (9.1 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10.7 g of compound 28. (Yield 71%, MS: [M+H)) + =630).

[0289] Synthesis Example 29. Synthesis of Compound 29

[0290]

[0291] Under a nitrogen atmosphere, compound CB (10 g, 23.9 mmol) and compound Trz8 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11 g of compound 29. (Yield 71%, MS: [M+H)) + =650).

[0292] Synthesis Example 30. Synthesis of Compound 30

[0293]

[0294] Under a nitrogen atmosphere, compound CB (10 g, 23.9 mmol) and compound Trz11 (8.7 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 9.7 g of compound 30. (Yield 66%, MS: [M+H)) + =613).

[0295] Synthesis Example 31. Synthesis of Compound 31

[0296]

[0297] Under a nitrogen atmosphere, compound CB (10 g, 23.9 mmol) and compound Trz26 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.3 g of compound 31. (Yield 73%, MS: [M+H)) + =650).

[0298] Synthesis Example 32. Synthesis of Compound 32

[0299]

[0300] Under a nitrogen atmosphere, compound CB (10 g, 23.9 mmol) and compound Trz27 (12.4 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 13.5 g of compound 32. (Yield 74%, MS: [M+H)) + =765).

[0301] Synthesis Example 33. Synthesis of Compound 33

[0302]

[0303] Under a nitrogen atmosphere, compound CC (10 g, 23.9 mmol) and compound Trz17 (6.5 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, stirred thoroughly, followed by bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol). 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 9.8 g of compound 33. (Yield 78%, MS: [M+H)) + =524).

[0304] Synthesis Example 34. Synthesis of Compound 34

[0305]

[0306] Under a nitrogen atmosphere, compound CC (10 g, 23.9 mmol) and compound Trz28 (8.7 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10 g of compound 34. (Yield 68%, MS: [M+H)) + =614).

[0307] Synthesis Example 35. Synthesis of Compound 35

[0308]

[0309] Under a nitrogen atmosphere, compound CD (10 g, 23.9 mmol) and compound Trz14 (8.7 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10 g of compound 35. (Yield 68%, MS: [M+H)) + =614).

[0310] Synthesis Example 36. Synthesis of Compound 36

[0311]

[0312] Under a nitrogen atmosphere, compound CD (10 g, 23.9 mmol) and compound Trz29 (9 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11 g of compound 36. (Yield 74%, MS: [M+H)) + =624).

[0313] Synthesis Example 37. Synthesis of Compound 37

[0314]

[0315] Under a nitrogen atmosphere, compound CD (10 g, 23.9 mmol) and compound Trz30 (9.6 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.5 g of compound 37. (Yield 74%, MS: [M+H)) + =650).

[0316] Synthesis Example 38. Synthesis of Compound 38

[0317]

[0318] Under a nitrogen atmosphere, compound CD (10 g, 23.9 mmol) and compound Trz17 (6.5 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10 g of compound 38. (Yield 80%, MS: [M+H)) + =524).

[0319] Synthesis Example 39. Synthesis of Compound 39

[0320]

[0321] Under a nitrogen atmosphere, compound CD (10 g, 23.9 mmol) and compound Trz31 (8.4 g, 24.4 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.9 g, 71.7 mmol) was dissolved in 30 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10 g of compound 39. (Yield 70%, MS: [M+H)) + =600).

[0322] Synthesis Example 40. Synthesis of Compound 40

[0323]

[0324] Under a nitrogen atmosphere, compound DA (10 g, 23 mmol) and compound Trz21 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11.2 g of compound 40. (Yield 73%, MS: [M+H)) + =666).

[0325] Synthesis Example 41. Synthesis of Compound 41

[0326]

[0327] Under a nitrogen atmosphere, compound DA (10 g, 23 mmol) and compound Trz30 (9.2 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 9.2 g of compound 41. (Yield 60%, MS: [M+H)) + =666).

[0328] Synthesis Example 42. Synthesis of Compound 42

[0329]

[0330] Under a nitrogen atmosphere, compound DA (10 g, 23 mmol) and compound Trz5 (7.5 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10.9 g of compound 42. (Yield 80%, MS: [M+H)) + =590).

[0331] Synthesis Example 43. Synthesis of Compound 43

[0332]

[0333] Under a nitrogen atmosphere, compound DB (10 g, 23 mmol) and compound Trz32 (10.4 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 12 g of compound 43. (Yield 73%, MS: [M+H)) + =716).

[0334] Synthesis Example 44. Synthesis of Compound 44

[0335]

[0336] Under a nitrogen atmosphere, compound DB (10 g, 23 mmol) and compound Trz33 (9.9 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 12.4 g of compound 44. (Yield 78%, MS: [M+H)) + =692).

[0337] Synthesis Example 45. Synthesis of Compound 45

[0338]

[0339] Under a nitrogen atmosphere, compound DB (10 g, 23 mmol) and compound Trz34 (11 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, stirred thoroughly, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol). 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 11.6 g of compound 45. (Yield 68%, MS: [M+H)) + =742).

[0340] Synthesis Example 46. Synthesis of Compound 46

[0341]

[0342] Under a nitrogen atmosphere, compound DB (10 g, 23 mmol) and compound Trz1 (8.1 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 11 g of compound 46. (Yield 78%, MS: [M+H)) + =616).

[0343] Synthesis Example 47. Synthesis of Compound 47

[0344]

[0345] Under a nitrogen atmosphere, compound DC (10 g, 23 mmol) and compound Trz35 (10.2 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 12 g of compound 47. (Yield 74%, MS: [M+H)) + =705).

[0346] Synthesis Example 48. Synthesis of Compound 48

[0347]

[0348] Under a nitrogen atmosphere, compound DC (10 g, 23 mmol) and compound Trz36 (10.2 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, stirred thoroughly, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol). 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 12.3 g of compound 48. (Yield 76%, MS: [M+H)) + =705).

[0349] Synthesis Example 49. Synthesis of Compound 49

[0350]

[0351] Under a nitrogen atmosphere, compound DC (10 g, 23 mmol) and compound Trz28 (8.4 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, stirred thoroughly, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol). 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 11.4 g of compound 49. (Yield 79%, MS: [M+H)) + =630).

[0352] Synthesis Example 50. Synthesis of Compound 50

[0353]

[0354] Under a nitrogen atmosphere, compound DD (10 g, 23 mmol) and compound Trz22 (8.1 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10.9 g of compound 50. (Yield 77%, MS: [M+H)) + =616).

[0355] Synthesis Example 51. Synthesis of Compound 51

[0356]

[0357] Under a nitrogen atmosphere, compound DD (10 g, 23 mmol) and compound Trz14 (8.4 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10 g of compound 51. (Yield 69%, MS: [M+H)) + =630).

[0358] Synthesis Example 52. Synthesis of Compound 52

[0359]

[0360] Under a nitrogen atmosphere, compound DD (10 g, 23 mmol) and compound Trz29 (8.6 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 10.6 g of compound 52. (Yield 72%, MS: [M+H)) + =640).

[0361] Synthesis Example 53. Synthesis of Compound 53

[0362]

[0363] Under a nitrogen atmosphere, compound DD (10 g, 23 mmol) and compound Trz5 (7.5 g, 23.5 mmol) were added to 200 mL of THF, stirred, and refluxed. Then, potassium carbonate (9.5 g, 69.1 mmol) was dissolved in 29 mL of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 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 9.6 g of compound 53. (Yield 71%, MS: [M+H)) + =590).

[0364] Example 1

[0365] 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.

[0366] 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.

[0367]

[0368] During the above process, the evaporation rate of organic matter is maintained. / seconds / second, lithium fluoride at the cathode maintains Evaporation rate of / second, aluminum maintains A vapor deposition rate of / second is achieved, while maintaining a vacuum level of 2×10⁻⁶ during vapor deposition. -7 Up to 5×10 -6 This led to the creation of organic light-emitting devices.

[0369] Examples 2 to 53

[0370] In the organic light-emitting device of Example 1, compounds 2 to 53 listed 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.

[0371]

[0372]

[0373]

[0374]

[0375] Comparative Examples 1 to 13

[0376] In the organic light-emitting device of Example 1, compound 1 was replaced with the compounds listed in Table 1 below, and the organic light-emitting device was otherwise manufactured by the same method as in Example 1 above. The compounds C-1 to C-13 used in Table 1 below are shown below.

[0377]

[0378] 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%.

[0379] [Table 1]

[0380]

[0381]

[0382]

[0383] When an electric current was applied to the organic light-emitting devices fabricated according to Examples 1 to 53 and Comparative Examples 1 to 13, the results shown in Table 1 were obtained. The red organic light-emitting device of Example 1, as described above, used conventionally widely used materials, 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 13, organic light-emitting devices were fabricated using compounds C-1 to C-13 instead of compound 1.

[0384] 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 a specific polycyclic structure 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 13 manufactured using the compounds of C-1 to C-13 described above. This demonstrates 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 53 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.

[0385] [Symbol Explanation]

[0386] 1: Substrate 2: Anode

[0387] 3: Light-emitting layer 4: Cathode

[0388] 5: Hole injection layer; 6: Hole transport layer

[0389] 7: Electron suppression layer; 8: Hole blocking layer

[0390] 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, One of the Ys is an O or an S, and the rest are single bonds. R1 is independently hydrogen; or deuterium. n1 and n2 are integers from 0 to 4. n3 is an integer from 0 to 3. R2 is represented by the following chemical formula 2. Chemical formula 2 In the chemical formula 2, L can be a single bond, phenylene, biphenylene, terphenylene, tetraphenylene, or naphthylene. X is always N, Ar1 and Ar2 are each independently phenyl, naphthyl-substituted phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, or phenyl-substituted carbazoyl.

2. The compound according to claim 1, wherein, The compound represented by chemical formula 1 is one of the compounds represented by any one of the following chemical formulas 1-1 to 1-8: Chemical Formula 1-1 Chemical formula 1-2 Chemical formulas 1-3 Chemical formulas 1-4 Chemical formulas 1-5 Chemical formulas 1-6 Chemical formulas 1-7 Chemical formulas 1-8 In the chemical formulas 1-1 to 1-8, Z is either O or S. R1, n1, n2, n3, L, X, Ar1, and Ar2 are the same as defined in claim 1.

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

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

5. 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 a compound according to any one of claims 1 to 4.

6. The organic light-emitting device according to claim 5, wherein, The organic layer containing the compound is a light-emitting layer.

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