organic light-emitting devices

Abstract

The present invention provides an organic light-emitting device.

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2019-0143627 filed on November 11, 2019 and Korean Patent Application No. 10-2020-0150020 filed on November 11, 2020, and incorporates all disclosures of the Korean patent applications into this specification.

[0003] The present invention relates to organic light emitting devices. Background Art

[0004] Organic light emitting diodes (OLEDs) are currently under extensive research due to their wide viewing angles, excellent contrast, and fast response times, as well as their superior brightness, drive voltage, and response speed.

[0005] Organic light-emitting devices typically have a structure comprising an anode, a cathode, and an organic layer positioned between the anode and cathode. To improve the efficiency and stability of organic light-emitting devices, these organic layers are often formed from multiple layers composed of different materials. For example, they can be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an organic light-emitting device structure, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed. When the excitons transition back to the ground state, light is emitted.

[0006] As for organic substances used in the organic light-emitting devices described above, there is a continuous demand for the development of new materials.

[0007] Prior art literature

[0008] Patent Literature

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

[0010] Technical issues

[0011] The present invention relates to organic light emitting devices.

[0012] Solution to the problem

[0013] The present invention provides the following organic light-emitting device, comprising:

[0014] anode;

[0015] a cathode disposed opposite to the anode; and

[0016] A light-emitting layer is provided between the anode and the cathode,

[0017] The light-emitting layer includes a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2:

[0018] [Chemical Formula 1]

[0019]

[0020] In the above Chemical Formula 1,

[0021] X is O or S,

[0022] L1 and L2 are each independently a single bond, or any one selected from the following groups,

[0023]

[0024] One of Ar1 and Ar2 is a substituted or unsubstituted C 6-60 Aryl, the other is substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 heteroaryl,

[0025] R is each independently hydrogen or deuterium,

[0026] a is an integer from 1 to 3,

[0027] b is an integer from 1 to 6,

[0028] [Chemical Formula 2]

[0029]

[0030] In the above chemical formula 2,

[0031] B1 to B4 are each independently C fused to an adjacent ring 6-60 Aromatic ring,

[0032] L'1 and L'2 are each independently a single bond; substituted or unsubstituted C 6-60 Arylene; or substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 Heteroarylene,

[0033] Ar'1 and Ar'2 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 heteroaryl,

[0034] R' is each independently hydrogen or deuterium,

[0035] c, d, e and f are each independently an integer from 1 to 6,

[0036] When a, b, c, d, e, and f each represent 2 or more, the substituents in the brackets may be the same as or different from each other.

[0037] Effects of the Invention

[0038] The organic light-emitting device comprises two host compounds in the light-emitting layer, thereby improving the efficiency, driving voltage and / or lifespan characteristics of the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figure 1 An example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a light-emitting layer 3 , and a cathode 4 is shown.

[0040] Figure 2 The diagram 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. DETAILED DESCRIPTION

[0041] Hereinafter, the present invention will be described in more detail to facilitate understanding.

[0042] or represents a bond to other substituents, D represents deuterium, and Ph represents phenyl.

[0043] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group ( Alkyl thioxy); arylthio ( Aryl thioxy); alkylsulfonyl ( Alkyl sulfoxy); arylsulfonyl ( The present invention also includes a silyl group, a boryl group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, or a heteroaryl group containing one or more N, O, and S atoms, or a substituent group consisting of two or more of the above-mentioned substituents linked together. For example, a "substituent group consisting of two or more substituents linked together" may be a biphenyl group. That is, a biphenyl group may be an aryl group, or it may be interpreted as a substituent group consisting of two phenyl groups linked together.

[0044] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, the group may have the following structure, but is not limited thereto.

[0045]

[0046] In the present specification, the oxygen of the ester group may be substituted by a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a group of the following structural formula, but is not limited thereto.

[0047]

[0048] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but preferably the number of carbon atoms is 1 to 25. Specifically, the group may have the following structure, but is not limited thereto.

[0049]

[0050] In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0051] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0052] In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

[0053] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of the alkyl group include, but are not limited to, 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, and 5-methylhexyl.

[0054] In the present specification, the alkenyl group may be linear 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 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-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbene, and styryl, but are not limited thereto.

[0055] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 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, there are 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, and adamantyl, but are not limited thereto.

[0056] In this specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, yl, fluorenyl, etc., but are not limited thereto.

[0057] In this specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. etc. However, the present invention is not limited thereto.

[0058] In the present specification, the heteroaryl group is a heterocyclic group containing one or more heteroatoms selected from O, N, Si and S as heteroatoms. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heteroaryl group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo[omicron] oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene Examples include, but are not limited to, oxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl.

[0059] In this specification, an aromatic ring refers to a fused monocyclic or polycyclic ring containing only carbon atoms as ring atoms and having aromaticity as the entire molecule. The number of carbon atoms in the aromatic ring is 6 to 60, or 6 to 30, or 6 to 20, but is not limited thereto. In addition, the aromatic ring may be a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, etc., but is not limited thereto.

[0060] In this specification, the aryl group in aralkyl, aralkenyl, alkylaryl, arylamine, and arylsilyl groups is the same as the examples for the aryl group described above. In this specification, the alkyl group in aralkyl, alkylaryl, and alkylamine groups is the same as the examples for the alkyl group described above. In this specification, the heteroaryl group in heteroarylamine is the same as the examples for the alkenyl group described above. In this specification, the arylene group is a divalent group, and the above description for aryl groups is applicable. In this specification, the heteroarylene group is a divalent group, and the above description for heteroaryl groups is applicable. In this specification, the hydrocarbon ring is not a monovalent group but is composed of two substituents bonded together, and the above description for aryl or cycloalkyl groups is applicable. In this specification, the heterocycle is not a monovalent group but is composed of two substituents bonded together, and the above description for heteroaryl groups is applicable.

[0061] In this specification, the term "deuterated or deuterium-substituted" means that at least one available hydrogen in each chemical formula has been replaced with deuterium. Specifically, in each chemical formula or substituent definition, deuterium-substituted means that at least one of the positions within the molecule where hydrogen can bind has been replaced with deuterium. More specifically, it means that at least 10% of the available hydrogens have been replaced with deuterium. As an example, at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, or 100% of the chemical formula is deuterated.

[0062] A light-emitting device is provided, comprising: an anode; a cathode disposed opposite the anode; and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer contains a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2.

[0063] The organic light-emitting device according to the present invention contains two compounds with specific structures as host substances in the light-emitting layer, thereby improving the efficiency, driving voltage and / or life characteristics of the organic light-emitting device.

[0064] Hereinafter, the present invention will be described in detail according to each configuration.

[0065] anode and cathode

[0066] The anode material is preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0067] The cathode material is preferably one with a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0068] hole injection layer

[0069] The organic light-emitting device according to the present invention may include a hole injection layer between the anode and the hole transport layer described later, as needed.

[0070] The hole injection layer is a layer located on the anode and injects holes from the anode, and contains a hole injection material. Such a hole injection material is preferably a compound that has the ability to transport holes, has the effect of injecting holes from the anode, has an excellent hole injection effect on 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 has excellent thin film forming ability. In particular, the HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer.

[0071] Specific examples of the hole-injecting material include metal porphyrin, oligothiophene, arylamine organic matter, hexanitrile hexaazatriphenylene organic matter, quinacridone organic matter, perylene organic matter, anthraquinone, polyaniline, and polythiophene conductive polymers, but are not limited thereto.

[0072] hole transport layer

[0073] The organic light-emitting device according to the present invention may include a hole transport layer between the anode and the light-emitting layer. The hole transport layer is a layer that receives holes from the anode or the hole injection layer formed on the anode and transports the holes to the light-emitting layer, and contains a hole transport substance. The hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. A substance with a high hole mobility is suitable. As specific examples, there are arylamine-based organic substances, conductive polymers, and block copolymers with both conjugated and non-conjugated parts, but the present invention is not limited to these.

[0074] electron blocking layer

[0075] The organic light-emitting device according to the present invention may, if desired, include an electron-blocking layer between the hole-transporting layer and the light-emitting layer. This electron-blocking layer is formed on the hole-transporting layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by regulating hole mobility and preventing excessive electron migration, thereby increasing the probability of hole-electron binding. The electron-blocking layer comprises an electron-blocking substance. Examples of such electron-blocking substances include, but are not limited to, arylamine-based organic substances.

[0076] light-emitting layer

[0077] The organic light-emitting device according to the present invention includes a light-emitting layer between an anode and a cathode. The light-emitting layer contains the first and second compounds as host materials. Specifically, the first compound functions as an N-type host material with superior electron-transporting ability over hole-transporting ability, while the second compound functions as a P-type host material with superior hole-transporting ability over electron-transporting ability. This maintains a suitable hole-to-electron ratio within the light-emitting layer. As a result, excitons emit light uniformly throughout the light-emitting layer, thereby simultaneously improving the luminous efficiency and lifespan of the organic light-emitting device.

[0078] Next, the first compound and the second compound will be described in sequence.

[0079] (First Compound)

[0080] The first compound is represented by Chemical Formula 1. Specifically, the first compound is a compound having a triazine group substituted in a furan / thiophene fused ring core fused to at least one side with a naphthalene ring. Compared to compounds having a triazine group substituted in a dibenzofuran / dibenzothiophene core, the first compound has excellent electron transport capability and effectively transfers electrons to the dopant substance, thereby increasing the probability of electron-hole recombination in the light-emitting layer.

[0081] Preferably, L1 can be a single bond,

[0082] In addition, L2 can be a single bond, or any one selected from the following groups:

[0083]

[0084] In contrast, in the case of compounds in Chemical Formula 1 where L2 does not have a linking group with the structure shown above, for example, compounds where L2 is 1,3-phenylene or 1,2-phenylene, exhibit poor stability toward electrons and holes compared to the first compound, making it difficult to effectively transfer energy to the dopant. Consequently, compared to organic light-emitting devices using the first compound as one of the co-hosts, compounds where L2 does not have a linking group with the structure shown above may exhibit inferior efficiency and lifespan characteristics.

[0085] Preferably, one of Ar1 and Ar2 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl or fluorenyl, and the other is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0086] Wherein, Ar1 and Ar2 may be unsubstituted or may be selected from deuterium, C 1-10 Alkyl and C 6-20 The aryl group is substituted by one or more substituents.

[0087] Specifically, Ar1 and Ar2 may each independently be a phenyl group, a deuterium-substituted phenyl group, a biphenyl group, a terphenyl group, a phenanthryl group, a naphthyl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, or a 9-phenylcarbazolyl group.

[0088] In addition, Ar1 and Ar2 may be the same as or different from each other.

[0089] In addition, one of Ar1 and Ar2 may be unsubstituted or may be a C substituted with deuterium. 6-20 Aryl.

[0090] In addition, Ar1 and Ar2 may both be unsubstituted, or may both be C substituted with deuterium. 6-20 Aryl.

[0091] Preferably, Ar1 is phenyl, biphenyl or naphthyl,

[0092] Ar2 can be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9-phenylcarbazolyl group or a carbazolyl group.

[0093] For example, Ar1 is any one selected from the following groups,

[0094]

[0095] Ar2 can be any one selected from the following groups:

[0096]

[0097] Preferably, each R is independently hydrogen or deuterium.

[0098] In addition, a representing the number of R may be 1, 2, or 3, and b may be 1, 2, 3, 4, 5, or 6.

[0099] Preferably, the first compound can be represented by any one of the following 1-1-1 to 1-1-3:

[0100] In the above chemical formulas 1-1-1 to 1-1-3,

[0101] X, L2, Ar1 and Ar2 are the same as defined in the above Chemical Formula 1.

[0102] Representative examples of the compound represented by the above Chemical Formula 1 are shown below:

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117] On the other hand, the compound represented by the above Chemical Formula 1, wherein Z is a substituent represented by the above Chemical Formula 1, can be produced by the production method shown in the following Reaction Formula 1:

[0118] [Reaction formula 1]

[0119]

[0120] In the above reaction formula 1, X" is a halogen, preferably bromine or chlorine, and the definitions of other substituents are the same as those described above.

[0121] Specifically, the compound represented by the above chemical formula 1 can be manufactured by Suzuki-coupling reaction of starting materials A1 and A2. Such Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group for the above Suzuki coupling reaction can be appropriately changed. The manufacturing method of the compound represented by the above chemical formula 1 can be more specifically described in the manufacturing example described later.

[0122] (Second Compound)

[0123] The second compound is represented by Chemical Formula 2. Specifically, the second compound has a biscarbazole structure, which can effectively transfer holes to the dopant material. Therefore, together with the first compound having excellent electron transport ability, it can increase the recombination probability of holes and electrons in the light-emitting layer.

[0124] B1 to B4 of the second compound may each independently be a benzene or naphthalene ring.

[0125] For example, B1 and B2 are each independently a benzene or naphthalene ring, and B3 and B4 can be a benzene ring. In this case, the second compound can be represented by the following chemical formula 2':

[0126] [Chemical Formula 2']

[0127]

[0128] In the above chemical formula 2',

[0129] B1 and B2 are each independently a benzene or naphthalene ring,

[0130] L'1, L'2, Ar'1, Ar'2, R', c and d are the same as defined in the above Chemical Formula 2.

[0131] Preferably, L'1 and L'2 can each independently be a single bond, or an unsubstituted or deuterated C 6-20 Arylene.

[0132] For example, L'1 and L'2 may each independently be a single bond, an unsubstituted or deuterium-substituted phenylene group, or an unsubstituted or deuterium-substituted naphthylene group.

[0133] For example, L'1 and L'2 can each independently be a single bond, or any one selected from the following groups:

[0134]

[0135] In this case, L'1 and L'2 may be the same as or different from each other.

[0136] Preferably, Ar'1 and Ar'2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluoranthenyl, fluorenyl, 9,9'-spirobifluorenyl, dibenzofuranyl or dibenzothiophenyl,

[0137] Wherein, Ar'1 and Ar'2 may be unsubstituted or may be selected from deuterium, C 1-10 Alkyl and C 6-20 The aryl group is substituted with one or more substituents, and the one or more substituents are, for example, one or two substituents.

[0138] For example, Ar'1 and Ar'2 can each independently be phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluoranthenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirobifluorenyl, dibenzofuranyl, or dibenzothiophenyl.

[0139] In addition, Ar'1 and Ar'2 may be the same as or different from each other.

[0140] In addition, R' may be all hydrogen or all deuterium.

[0141] Furthermore, c, d, e, and f representing the number of R' may each independently be an integer of 1 to 6. As an example, when B1 and B2 are benzene rings, c and d each independently are an integer of 1 to 4, when B1 and B2 are naphthalene rings, c and d each independently are an integer of 1 to 6, when B3 and B4 are benzene rings, e and f each independently are an integer of 1 to 3, when B3 and B4 are naphthalene rings, e and f each independently are an integer of 1 to 5.

[0142] On the other hand, when B1 to B4 are all benzene rings, the second compound can be represented by the following chemical formula 2-1:

[0143]

[0144] In the above chemical formula 2-1,

[0145] L'1, L'2, Ar'1, and Ar'2 are the same as defined in the above Chemical Formula 2.

[0146] In addition, when B1 is a naphthalene ring and B2 to B4 are all benzene rings, the second compound can be represented by the following chemical formulas 2-2 to 2-4:

[0147]

[0148] In the above chemical formulas 2-1 to 2-4,

[0149] L'1, L'2, Ar'1, and Ar'2 are the same as defined in the above Chemical Formula 2.

[0150] In addition, when B1 and B2 are naphthalene rings, and B3 and B4 are benzene rings, the second compound can be represented by the following chemical formulas 2-5 to 2-10:

[0151]

[0152] In the above Chemical Formulas 2-5 to 2-10,

[0153] L'1, L'2, Ar'1, and Ar'2 are the same as defined in the above Chemical Formula 2.

[0154] Representative examples of the compound represented by the above Chemical Formula 2 are shown below:

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] On the other hand, as an example, the compound represented by the above Chemical Formula 2 can be produced by the production method shown in the following Reaction Formula 2:

[0177] [Reaction formula 2]

[0178]

[0179] In the above reaction formula 2, X" is a halogen, preferably bromine or chlorine, and the definitions of other substituents are the same as those described above.

[0180] Specifically, the compound represented by the above chemical formula 2 can be manufactured by Suzuki coupling reaction of starting materials A3 and A4. Such Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the above Suzuki coupling reaction can be appropriately changed. The manufacturing method of the compound represented by the above chemical formula 2 can be further specified in the manufacturing examples described later.

[0181] The first compound and the second compound may be contained in the light-emitting layer at a weight ratio of 1:99 to 99:1. In this case, in order to appropriately maintain the ratio of holes to electrons in the light-emitting layer, the first compound and the second compound are preferably contained in a weight ratio of 30:70 to 70:30.

[0182] On the other hand, the above-mentioned light-emitting layer may contain a dopant substance in addition to the above-mentioned two host substances. Such dopant substances include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, Styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetramine. Furthermore, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0183] More specifically, as the dopant material, the following compounds may be used, but are not limited thereto:

[0184]

[0185]

[0186]

[0187]

[0188] hole blocking layer

[0189] The organic light-emitting device according to the present invention may include a hole blocking layer between the light-emitting layer and the electron transport layer described later as needed. The hole blocking layer refers to a layer formed on the light-emitting layer, preferably in contact with the light-emitting layer, which improves the efficiency of the organic light-emitting device by adjusting the electron mobility and preventing the excessive migration of holes to increase the hole-electron binding rate. The hole blocking layer contains a hole blocking substance. As examples of such hole blocking substances, azine derivatives containing triazine, triazole derivatives, Compounds into which electron-withdrawing groups are introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, and the like.

[0190] Electron injection and transport layer

[0191] The electron injection and transport layer is a layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer, and plays the role of both an electron transport layer and an electron injection layer, and is formed on the light-emitting layer or the hole blocking layer. Such electron injection and transport substances are substances that can well inject electrons from the cathode and transfer them to the light-emitting layer, and substances with high electron mobility are suitable. Specific examples of electron injection and transport substances include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc., but are not limited to these. Alternatively, it can also be combined with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and the like, as well as their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, are used together, but are not limited thereto.

[0192] The electron injection and transport layer can also be formed as an independent layer such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the light-emitting layer or the hole blocking layer, and as the electron transport material contained in the electron transport layer, the electron injection and transport material can be used. In addition, the electron injection layer is formed on the electron transport layer, and as the electron injection material contained in the electron injection layer, LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, etc. and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, etc.

[0193] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)gallium chloride, bis(2-methyl-8-quinolinato)(o-cresol)gallium, bis(2-methyl-8-quinolinato)(1-naphthol)aluminum, and bis(2-methyl-8-quinolinato)(2-naphthol)gallium.

[0194] organic light-emitting devices

[0195] The structure of the organic light emitting device according to the present invention is shown in FIG. Figure 1 . Figure 1 The figure shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the above structure, the first compound and the second compound may be contained in the light-emitting layer.

[0196] Figure 2 The diagram 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.

[0197] In the above structure, the first compound and the second compound may be contained in the light-emitting layer.

[0198] The organic light-emitting device according to the present invention can be manufactured by sequentially stacking the above-mentioned structures. In this case, it can be manufactured as follows: a metal or a conductive metal oxide or an alloy thereof is vapor-deposited on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, and then the above-mentioned layers are formed on the anode, and then a substance that can be used as a cathode is vapor-deposited thereon to manufacture it. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode material, an organic layer, and an anode material on a substrate. In addition, not only a vacuum evaporation method but also a solution coating method can be used to form a main body and a dopant into a light-emitting layer. Here, the so-called solution coating method refers to a spin coating method, a dip coating method, a doctor blade method, an inkjet printing method, a screen printing method, a spray method, a roller coating method, etc., but is not limited to these.

[0199] In addition to these methods, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003 / 012890). However, the manufacturing method is not limited to this.

[0200] On the other hand, the organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type depending on the materials used.

[0201] The production of the organic light-emitting device is specifically described in the following examples. However, the following examples are provided to illustrate the present invention and the scope of the present invention is not limited thereto.

[0202] [Synthesis Example of the First Compound]

[0203] Synthesis Example 1: Preparation of Compound 1

[0204]

[0205] Under a nitrogen atmosphere, substance (sub) 1 (15 g, 40.8 mmol) and chemical formula A (11.8 g, 44.9 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (16.9 g, 122.3 mmol) was dissolved in 51 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.6 g of compound 1.

[0206] (yield 65%, MS: [M+H] + =550)

[0207] Synthesis Example 2: Preparation of Compound 2

[0208]

[0209] Under a nitrogen atmosphere, substance 2 (15 g, 47.2 mmol) and chemical formula A (13.6 g, 51.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (19.6 g, 141.6 mmol) was then dissolved in 59 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 10 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.4 g of compound 2.

[0210] (yield 61%, MS: [M+H] + =500)

[0211] Synthesis Example 3: Preparation of Compound 3

[0212]

[0213] Under a nitrogen atmosphere, substance 3 (15 g, 38.1 mmol) and chemical formula A (11 g, 41.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (15.8 g, 114.3 mmol) was then dissolved in 47 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.4 g of compound 3.

[0214] (yield 61%, MS: [M+H] + =576)

[0215] Synthesis Example 4: Preparation of Compound 4

[0216]

[0217] Under a nitrogen atmosphere, substance 4 (15 g, 43.6 mmol) and chemical formula A (12.6 g, 48 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.1 g, 130.9 mmol) was then dissolved in 54 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.3 g of compound 4.

[0218] (yield 80%, MS: [M+H] + =526)

[0219] Synthesis Example 5: Preparation of Compound 5

[0220]

[0221] Under a nitrogen atmosphere, substance 5 (15 g, 35.7 mmol) and chemical formula A (10.3 g, 39.3 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.8 g, 107.2 mmol) was then dissolved in 44 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 5.

[0222] (yield 71%, MS: [M+H] + =602)

[0223] Synthesis Example 6: Preparation of Compound 6

[0224]

[0225] Under a nitrogen atmosphere, substance 6 (15 g, 35.9 mmol) and chemical formula A (10.3 g, 39.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.9 g, 107.7 mmol) was then dissolved in 45 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.1 g of compound 6.

[0226] (yield 61%, MS: [M+H] + =600)

[0227] Synthesis Example 7: Preparation of Compound 7

[0228]

[0229] Under a nitrogen atmosphere, substance 7 (15 g, 35.7 mmol) and chemical formula A (10.3 g, 39.3 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.8 g, 107.2 mmol) was then dissolved in 44 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of compound 7.

[0230] (yield 66%, MS: [M+H] + =602)

[0231] Synthesis Example 8: Preparation of Compound 8

[0232]

[0233] Under a nitrogen atmosphere, substance 8 (15 g, 40.8 mmol) and chemical formula A (11.8 g, 44.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (16.9 g, 122.3 mmol) was then dissolved in 51 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.4 g of compound 8.

[0234] (yield 60%, MS: [M+H] + =550)

[0235] Synthesis Example 9: Preparation of Compound 9

[0236]

[0237] Under a nitrogen atmosphere, substance 9 (15 g, 40.8 mmol) and chemical formula A (11.8 g, 44.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (16.9 g, 122.3 mmol) was then dissolved in 51 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.1 g of compound 9.

[0238] (yield 63%, MS: [M+H] + =550)

[0239] Synthesis Example 10: Preparation of Compound 10

[0240]

[0241] Under a nitrogen atmosphere, substance 10 (15 g, 38.1 mmol) and chemical formula A (11 g, 41.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (15.8 g, 114.3 mmol) was then dissolved in 47 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.8 g of compound 10.

[0242] (yield 72%, MS: [M+H] + =576)

[0243] Synthesis Example 11: Preparation of Compound 11

[0244]

[0245] Under a nitrogen atmosphere, substance 11 (15 g, 38.1 mmol) and chemical formula A (11 g, 41.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (15.8 g, 114.3 mmol) was then dissolved in 47 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.6 g of compound 11.

[0246] (yield 76%, MS: [M+H] + =576)

[0247] Synthesis Example 12: Preparation of Compound 12

[0248]

[0249] Under a nitrogen atmosphere, substance 12 (15 g, 41.9 mmol) and chemical formula A (12.1 g, 46.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (17.4 g, 125.8 mmol) was then dissolved in 52 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.8 g of compound 12.

[0250] (yield 61%, MS: [M+H] + =540)

[0251] Synthesis Example 13: Preparation of Compound 13

[0252]

[0253] Under a nitrogen atmosphere, substance 13 (15 g, 41.9 mmol) and chemical formula A (12.1 g, 46.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (17.4 g, 125.8 mmol) was then dissolved in 52 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.4 g of compound 13.

[0254] (yield 68%, MS: [M+H] + =540)

[0255] Synthesis Example 14: Preparation of Compound 14

[0256]

[0257] Under a nitrogen atmosphere, substance 14 (15 g, 36.8 mmol) and chemical formula A (10.6 g, 40.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (15.2 g, 110.3 mmol) was then dissolved in 46 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 11 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.3 g of compound 14.

[0258] (yield 75%, MS: [M+H] + =590)

[0259] Synthesis Example 15: Preparation of Compound 15

[0260]

[0261] Under a nitrogen atmosphere, substance 15 (15 g, 36.8 mmol) and chemical formula A (10.6 g, 40.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (15.2 g, 110.3 mmol) was then dissolved in 46 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 15.

[0262] (yield 70%, MS: [M+H] + =590)

[0263] Synthesis Example 16: Preparation of Compound 16

[0264]

[0265] Under a nitrogen atmosphere, substance 16 (15 g, 40.1 mmol) and chemical formula A (11.6 g, 44.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (16.6 g, 120.4 mmol) was then dissolved in 50 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.8 g of compound 16.

[0266] (yield 62%, MS: [M+H] + =556)

[0267] Synthesis Example 17: Preparation of Compound 17

[0268]

[0269] Under a nitrogen atmosphere, substance 17 (15 g, 40.1 mmol) and chemical formula A (11.6 g, 44.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (16.6 g, 120.4 mmol) was then dissolved in 50 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.1 g of compound 17.

[0270] (yield 68%, MS: [M+H] + =556)

[0271] Synthesis Example 18: Preparation of Compound 18

[0272]

[0273] Under a nitrogen atmosphere, substance 18 (15 g, 40.1 mmol) and chemical formula A (11.6 g, 44.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (16.6 g, 120.4 mmol) was then dissolved in 50 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.8 g of compound 18.

[0274] (yield 80%, MS: [M+H] + =556)

[0275] Synthesis Example 19: Preparation of Compound 19

[0276]

[0277] Under a nitrogen atmosphere, substance 19 (15 g, 34.6 mmol) and chemical formula A (10 g, 38.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.4 g, 103.9 mmol) was then dissolved in 43 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 10 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.5 g of compound 19.

[0278] (yield 73%, MS: [M+H] + =615)

[0279] Synthesis Example 20: Preparation of Compound 20

[0280]

[0281] Under a nitrogen atmosphere, substance 20 (15 g, 34.6 mmol) and chemical formula A (10 g, 38.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.4 g, 103.9 mmol) was then dissolved in 43 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 11 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17 g of compound 20.

[0282] (yield 80%, MS: [M+H] + =61)

[0283] Synthesis Example 21: Preparation of Compound 21

[0284]

[0285] Under a nitrogen atmosphere, substance 21 (15 g, 42 mmol) and chemical formula A (12.1 g, 46.2 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (17.4 g, 126.1 mmol) was then dissolved in 52 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.5 g of compound 21.

[0286] (yield 64%, MS: [M+H] + =539)

[0287] Synthesis Example 22: Preparation of Compound 22

[0288]

[0289] Under a nitrogen atmosphere, substance 22 (15 g, 31.1 mmol) and chemical formula A (9 g, 34.2 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12.9 g, 93.2 mmol) was then dissolved in 39 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 11 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 22.

[0290] (yield 60%, MS: [M+H] + =665)

[0291] Synthesis Example 23: Preparation of Compound 23

[0292]

[0293] (1) Step 23-1: Preparation of intermediate compound substance B-1

[0294] Under a nitrogen atmosphere, substance 2 (15 g, 47.2 mmol) and chemical formula B (7.4 g, 47.2 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (19.6 g, 141.6 mmol) was then dissolved in 59 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.9 g of substance B-1.

[0295] (yield 75%, MS: [M+H] + =394)

[0296] (2) Step 23-2: Preparation of Compound 23

[0297] Under a nitrogen atmosphere, substance B-1 (15 g, 38.1 mmol) and chemical formula A (11 g, 41.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (15.8 g, 114.3 mmol) was then dissolved in 47 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.3 g of compound 23.

[0298] (yield 70%, MS: [M+H] + =576)

[0299] Synthesis Example 24: Preparation of Compound 24

[0300]

[0301] (1) Step 24-1: Preparation of intermediate compound substance B-2

[0302] Under a nitrogen atmosphere, substance 23 (15 g, 35.7 mmol) and chemical formula B (5.6 g, 35.7 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.8 g, 107.2 mmol) was then dissolved in 44 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12 g of substance B-2.

[0303] (yield 68%, MS: [M+H] + =496)

[0304] (2) Step 24-2: Preparation of Compound 24

[0305] Under a nitrogen atmosphere, substance B-2 (15 g, 30.2 mmol) and chemical formula A (8.7 g, 33.3 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12.5 g, 90.7 mmol) was then dissolved in 38 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.1 g of compound 24.

[0306] (yield 64%, MS: [M+H] + =678)

[0307] Synthesis Example 25: Preparation of Compound 25

[0308]

[0309] (1) Step 25-1: Preparation of intermediate compound substance B-3

[0310] Under a nitrogen atmosphere, substance 12 (15 g, 41.9 mmol) and chemical formula B (6.6 g, 41.9 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.9 g of substance B-3.

[0311] (yield 71%, MS: [M+H] + =434)

[0312] (2) Step 25-2: Preparation of Compound 25

[0313] Under a nitrogen atmosphere, substance B-3 (15 g, 34.6 mmol) and chemical formula A (10 g, 38 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.3 g, 103.7 mmol) was then dissolved in 43 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17 g of compound 25.

[0314] (yield 80%, MS: [M+H] + =616)

[0315] Synthesis Example 26: Preparation of Compound 26

[0316]

[0317] (1) Step 26-1: Preparation of intermediate compound substance B-4

[0318] Under a nitrogen atmosphere, substance 17 (15 g, 40.1 mmol) and chemical formula B (6.3 g, 40.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (16.6 g, 120.4 mmol) was then dissolved in 50 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.1 g of substance B-4.

[0319] (yield 67%, MS: [M+H] + =450)

[0320] (2) Step 26-2: Preparation of Compound 26

[0321] Under a nitrogen atmosphere, substance B-4 (15 g, 33.3 mmol) and chemical formula A (9.6 g, 36.7 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (13.8 g, 100 mmol) was then dissolved in 41 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 11 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.8 g of compound 26.

[0322] (yield 75%, MS: [M+H] + =632)

[0323] Synthesis Example 27: Preparation of Compound 27

[0324]

[0325] (1) Step 27-1: Preparation of intermediate compound substance B-5

[0326] Under a nitrogen atmosphere, substance 3 (15 g, 38.1 mmol) and chemical formula A (10 g, 38.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (15.8 g, 114.3 mmol) was then dissolved in 47 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0) (0.4 g, 0.4 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.1 g of substance B-5.

[0327] (yield 79%, MS: [M+H] + =470)

[0328] (2) Step 27-2: Preparation of Compound 27

[0329] Under a nitrogen atmosphere, substance B-5 (15 g, 31.9 mmol) and chemical formula A (9.2 g, 35.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (13.2 g, 95.8 mmol) was then dissolved in 40 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 10 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.5 g of compound 27.

[0330] (yield 60%, MS: [M+H] + =652)

[0331] Synthesis Example 28: Preparation of Compound 28

[0332]

[0333] (1) Step 28-1: Preparation of intermediate compound B-6

[0334] Under a nitrogen atmosphere, substance 24 (15 g, 35.4 mmol) and chemical formula B (5.5 g, 35.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.7 g, 106.2 mmol) was then dissolved in 44 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.4 mmol) was added. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.5 g of substance B-6.

[0335] (yield 71%, MS: [M+H] + =500)

[0336] (2) Step 28-2: Preparation of Compound 28

[0337] Under a nitrogen atmosphere, substance B-6 (15 g, 30 mmol) and chemical formula A (8.6 g, 33 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (12.4 g, 90 mmol) was dissolved in 37 mL of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.9 g of compound 28. (Yield 73%, MS: [M+H] + =682)

[0338] Synthesis Example 29: Preparation of Compound 29

[0339]

[0340] (1) Step 29-1: Preparation of intermediate compound C-1

[0341] Under a nitrogen atmosphere, substance 25 (15 g, 56 mmol) and chemical formula C (11.6 g, 56 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in 70 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.7 g of substance C-1.

[0342] (yield 76%, MS: [M+H] + =394)

[0343] (2) Step 29-2: Preparation of Compound 29

[0344] Under a nitrogen atmosphere, substance C-1 (15 g, 38.1 mmol) and chemical formula A (10 g, 38.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (15.8 g, 114.3 mmol) was then dissolved in 47 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was put into the mixture. After reacting for 11 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16 g of compound 29.

[0345] (yield 73%, MS: [M+H] + =576)

[0346] Synthesis Example 30: Preparation of Compound 30

[0347]

[0348] (1) Step 30-1: Preparation of intermediate compound C-2

[0349] Under a nitrogen atmosphere, substance 2 (15 g, 47.2 mmol) and chemical formula C (9.7 g, 47.2 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (19.6 g, 141.6 mmol) was then dissolved in 59 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14 g of substance C-2.

[0350] (yield 67%, MS: [M+H] + =444)

[0351] (2) Step 30-2: Preparation of Compound 30

[0352] Under a nitrogen atmosphere, substance C-2 (15 g, 33.8 mmol) and chemical formula A (8.9 g, 33.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14 g, 101.4 mmol) was then dissolved in 42 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.1 g of compound 30.

[0353] (yield 62%, MS: [M+H] + =626)

[0354] Synthesis Example 31: Preparation of Compound 31

[0355]

[0356] (1) Step 31-1: Preparation of intermediate compound C-3

[0357] Under a nitrogen atmosphere, substance 26 (15 g, 40.8 mmol) and chemical formula C (8.4 g, 40.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (16.9 g, 122.3 mmol) was dissolved in 51 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.5 g of substance C-3. (Yield 67%, MS: [M+H] + =494)

[0358] (2) Step 31-2: Preparation of Compound 31

[0359] Under a nitrogen atmosphere, substance C-3 (15 g, 30.4 mmol) and chemical formula A (8 g, 30.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12.6 g, 91.1 mmol) was then dissolved in 38 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 10 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.6 g of compound 31.

[0360] (yield 76%, MS: [M+H] + =676)

[0361] Synthesis Example 32: Preparation of Compound 32

[0362]

[0363] (1) Step 32-1: Preparation of intermediate compound C-4

[0364] Under a nitrogen atmosphere, substance 4 (15 g, 43.6 mmol) and chemical formula C (9 g, 43.6 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (18.1 g, 130.9 mmol) was then dissolved in 54 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.4 g of substance C-4.

[0365] (yield 80%, MS: [M+H] + =470)

[0366] (2) Step 32-2: Preparation of Compound 32

[0367] Under a nitrogen atmosphere, substance C-4 (15 g, 31.9 mmol) and chemical formula A (8.4 g, 31.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (13.2 g, 95.8 mmol) was then dissolved in 40 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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.

[0368] (yield 65%, MS: [M+H] + =652)

[0369] Synthesis Example 33: Preparation of Compound 33

[0370]

[0371] (1) Step 33-1: Preparation of intermediate compound C-5

[0372] Under a nitrogen atmosphere, substance 10 (15 g, 38.1 mmol) and chemical formula C (7.9 g, 38.1 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of substance C-5. (Yield 72%, MS: [M+H] + =520)

[0373] (2) Step 33-2: Preparation of Compound 33

[0374] Under a nitrogen atmosphere, substance C-5 (15 g, 28.8 mmol) and chemical formula A (7.6 g, 28.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12 g, 86.5 mmol) was then dissolved in 36 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.1 g of compound 33.

[0375] (yield 60%, MS: [M+H] + =702)

[0376] Synthesis Example 34: Preparation of Compound 34

[0377]

[0378] (1) Step 34-1: Preparation of intermediate compound C-6

[0379] Under a nitrogen atmosphere, substance 27 (15 g, 40.8 mmol) and chemical formula C (8.4 g, 40.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (16.9 g, 122.3 mmol) was then dissolved in 51 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.7 g of substance C-6.

[0380] (yield 78%, MS: [M+H] + =494)

[0381] (2) Step 34-2: Preparation of Compound 34

[0382] Under a nitrogen atmosphere, substance C-6 (15 g, 30.4 mmol) and chemical formula A (8 g, 30.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12.6 g, 91.1 mmol) was then dissolved in 38 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 10 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 34.

[0383] (yield 74%, MS: [M+H] + =676)

[0384] Synthesis Example 35: Preparation of Compound 35

[0385]

[0386] (1) Step 35-1: Preparation of intermediate compound C-7

[0387] Under a nitrogen atmosphere, substance 34 (15 g, 39.1 mmol) and chemical formula C (8.1 g, 39.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (16.2 g, 117.2 mmol) was then dissolved in 49 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.9 g of substance C-7.

[0388] (yield 80%, MS: [M+H] + =510)

[0389] (2) Step 35-2: Preparation of Compound 35

[0390] Under a nitrogen atmosphere, substance C-7 (15 g, 29.4 mmol) and chemical formula A (7.7 g, 29.4 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12.2 g, 88.2 mmol) was then dissolved in 37 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of compound 35.

[0391] (yield 70%, MS: [M+H] + =692)

[0392] Synthesis Example 36: Preparation of Compound 36

[0393]

[0394] (1) Step 36-1: Preparation of intermediate compound C-8

[0395] Under a nitrogen atmosphere, substance 28 (15 g, 34.6 mmol) and chemical formula C (7.2 g, 34.6 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (14.4 g, 103.9 mmol) was dissolved in 43 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.3 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.3 g of substance C-8.

[0396] (yield 69%, MS: [M+H] + =559)

[0397] (2) Step 36-2: Preparation of Compound 36

[0398] Under a nitrogen atmosphere, substance C-8 (15 g, 26.8 mmol) and chemical formula A (7 g, 26.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.1 g, 80.5 mmol) was then dissolved in 33 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.5 g of compound 36.

[0399] (yield 78%, MS: [M+H] + =741)

[0400] Synthesis Example 37: Preparation of Compound 37

[0401]

[0402] (1) Step 37-1: Preparation of intermediate compound C-9

[0403] Under a nitrogen atmosphere, substance 19 (15 g, 34.6 mmol) and chemical formula C (7.2 g, 34.6 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.4 g, 103.9 mmol) was then dissolved in 43 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.3 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.9 g of substance C-9.

[0404] (yield 72%, MS: [M+H] + =559)

[0405] (2) Step 37-2: Preparation of Compound 37

[0406] Under a nitrogen atmosphere, substance C-9 (15 g, 26.8 mmol) and chemical formula A (7 g, 26.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.1 g, 80.5 mmol) was then dissolved in 33 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture. After reacting for 11 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.5 g of compound 37.

[0407] (yield 73%, MS: [M+H] + =741)

[0408] Synthesis Example 38: Preparation of Compound 38

[0409]

[0410] (1) Step 38-1: Preparation of intermediate compound C-10

[0411] Under a nitrogen atmosphere, substance 12 (15 g, 41.9 mmol) and chemical formula C (8.7 g, 41.9 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (17.4 g, 125.8 mmol) was then dissolved in 52 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of substance C-10.

[0412] (yield 70%, MS: [M+H] + =484)

[0413] (2) Step 38-2: Preparation of Compound 38

[0414] Under a nitrogen atmosphere, substance C-10 (15 g, 31 mmol) and chemical formula A (8.1 g, 31 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12.9 g, 93 mmol) was then dissolved in 39 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 10 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.4 g of compound 38.

[0415] (yield 65%, MS: [M+H] + =666)

[0416] Synthesis Example 39: Preparation of Compound 39

[0417]

[0418] (1) Step 39-1: Preparation of intermediate compound C-11

[0419] Under a nitrogen atmosphere, substance 14 (15 g, 36.8 mmol) and chemical formula C (7.6 g, 36.8 mmol) were added to 300 mL of THF, stirred and refluxed. Then, potassium carbonate (15.2 g, 110.3 mmol) was dissolved in 46 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.9 g of substance C-11.

[0420] (yield 66%, MS: [M+H] + =534)

[0421] (2) Step 39-2: Preparation of Compound 39

[0422] Under a nitrogen atmosphere, substance C-11 (15 g, 28.1 mmol) and chemical formula A (7.4 g, 28.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.6 g, 84.3 mmol) was then dissolved in 35 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.5 g of compound 39.

[0423] (yield 72%, MS: [M+H] + =716)

[0424] Synthesis Example 40: Preparation of Compound 40

[0425]

[0426] (1) Step 40-1: Preparation of intermediate compound C-12

[0427] Under a nitrogen atmosphere, substance 29 (15 g, 36.8 mmol) and chemical formula C (7.6 g, 36.8 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (15.2 g, 110.3 mmol) was then dissolved in 46 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.9 g of substance C-12.

[0428] (yield 66%, MS: [M+H] + =534)

[0429] (2) Step 40-2: Preparation of Compound 40

[0430] Under a nitrogen atmosphere, substance C-12 (15 g, 28.1 mmol) and chemical formula A (7.4 g, 28.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.6 g, 84.3 mmol) was then dissolved in 35 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture. After reacting for 9 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.7 g of compound 40.

[0431] (yield 63%, MS: [M+H] + =716)

[0432] Synthesis Example 41: Preparation of Compound 41

[0433]

[0434] (1) Step 41-1: Preparation of intermediate compound C-13

[0435] Under a nitrogen atmosphere, substance 30 (15 g, 35.5 mmol) and chemical formula C (7.3 g, 35.5 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (14.7 g, 106.4 mmol) was then dissolved in 44 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.4 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.6 g of substance C-13.

[0436] (yield 75%, MS: [M+H] + =550)

[0437] (2) Step 41-2: Preparation of Compound 41

[0438] Under a nitrogen atmosphere, substance C-13 (15 g, 27.3 mmol) and chemical formula A (7.1 g, 27.3 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (11.3 g, 81.8 mmol) was then dissolved in 34 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.6 g of compound 41.

[0439] (yield 68%, MS: [M+H] + =732)

[0440] Synthesis Example 42: Preparation of Compound 42

[0441]

[0442] (1) Step 42-1: Preparation of intermediate compound C-14

[0443] Under a nitrogen atmosphere, substance 17 (15 g, 40.1 mmol) and chemical formula C (8.3 g, 40.1 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (16.6 g, 120.4 mmol) was then dissolved in 50 mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13 g of substance C-14.

[0444] (yield 65%, MS: [M+H] + =500)

[0445] (2) Step 42-2: Preparation of Compound 42

[0446] Under a nitrogen atmosphere, substance C-14 (15 g, 30 mmol) and chemical formula A (7.9 g, 30 mmol) were added to 300 mL of THF, stirred and refluxed. Potassium carbonate (12.4 g, 90 mmol) was then dissolved in 37 mL of water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was put into the mixture. After reacting for 8 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.7 g of compound 42.

[0447] (yield 72%, MS: [M+H] + =682)

[0448] [Synthesis Example of the Second Compound]

[0449] Synthesis Example 2-1: Preparation of Compound 2-1

[0450]

[0451] Under a nitrogen atmosphere, intermediate 2-1-1 (10 g, 25.2 mmol) and intermediate 2-1-2 (8 g, 27.7 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and put into the reaction mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the reaction mixture during reflux. After reacting for 3 hours, the reaction mixture was cooled to room temperature, the organic layer was separated from the aqueous layer, and the organic layer was distilled. The reaction mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9 g of compound 2-1.

[0452] (yield 64%, MS: [M+H] + =561)

[0453] Synthesis Example 2-2: Preparation of Compound 2-2

[0454]

[0455] Under a nitrogen atmosphere, intermediate 2-2-1 (10 g, 25.2 mmol) and intermediate 2-2-2 (8 g, 27.7 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture during reflux. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 2-2.

[0456] (yield 66%, MS: [M+H] + =637)

[0457] Synthesis Example 2-3: Preparation of Compound 2-3

[0458]

[0459] Under a nitrogen atmosphere, intermediate 2-3-1 (10 g, 25.2 mmol) and intermediate 2-3-2 (10.1 g, 27.7 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and put into the reaction mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the reaction mixture during reflux. After reacting for 4 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The reaction mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9 g of compound 2-3.

[0460] (yield 56%, MS: [M+H] + =637)

[0461] Synthesis Example 2-4: Preparation of Compound 2-4

[0462]

[0463] Under a nitrogen atmosphere, intermediate 2-4-1 (10 g, 25.2 mmol) and intermediate 2-4-2 (9.3 g, 27.7 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture during reflux. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 2-4.

[0464] (yield 51%, MS: [M+H] + =611)

[0465] Synthesis Example 2-5: Preparation of Compound 2-5

[0466]

[0467] Under a nitrogen atmosphere, intermediate 2-5-1 (10 g, 25.2 mmol) and intermediate 2-5-2 (10.1 g, 27.7 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture during reflux. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.4 g of compound 2-5.

[0468] (yield 65%, MS: [M+H] + =637)

[0469] Synthesis Example 2-6: Preparation of Compound 2-6

[0470]

[0471] Under a nitrogen atmosphere, intermediate 2-6-1 (10 g, 25.2 mmol) and intermediate 2-6-2 (11.4 g, 27.7 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture during reflux. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.5 g of compound 2-6.

[0472] (yield 61%, MS: [M+H] + =687)

[0473] Synthesis Example 2-7: Preparation of Compound 2-7

[0474]

[0475] Under a nitrogen atmosphere, intermediate 2-7-1 (10 g, 22.4 mmol) and intermediate 2-7-2 (10.2 g, 24.6 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (12.4 g, 89.5 mmol) was dissolved in water and put into the reaction mixture. After sufficient stirring, bis(tri-tert-butylphosphine) palladium (0) (0.1 g, 0.2 mmol) was put into the reaction mixture during reflux. After reacting for 3 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The reaction mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11 g of compound 2-7.

[0476] (yield 67%, MS: [M+H] + =737)

[0477] Synthesis Example 2-8: Preparation of Compound 2-8

[0478]

[0479] Under a nitrogen atmosphere, intermediate 2-8-1 (10 g, 17.9 mmol) and intermediate 2-8-2 (5.6 g, 19.7 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (9.9 g, 71.5 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 2-8.

[0480] (yield 60%, MS: [M+H] + =723)

[0481] Synthesis Example 2-9: Preparation of Compound 2-9

[0482]

[0483] Under a nitrogen atmosphere, intermediate 2-9-1 (10 g, 21.1 mmol) and intermediate 2-9-2 (6.7 g, 23.3 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (11.7 g, 84.6 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 7.4 g of compound 2-9.

[0484] (yield 55%, MS: [M+H] + =637)

[0485] Synthesis Example 2-10: Preparation of Compound 2-10

[0486]

[0487] Under a nitrogen atmosphere, intermediate 2-10-1 (10 g, 27 mmol) and intermediate 2-10-2 (10 g, 29.6 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (14.9 g, 107.8 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture during reflux. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11 g of compound 2-10.

[0488] (yield 70%, MS: [M+H] + =585)

[0489] Synthesis Example 2-11: Preparation of Compound 2-11

[0490]

[0491] Under a nitrogen atmosphere, intermediate 2-11-1 (10 g, 27 mmol) and intermediate 2-11-2 (11.5 g, 29.6 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (14.9 g, 107.8 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was put into the mixture during reflux. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 2-11.

[0492] (yield 67%, MS: [M+H] + =635)

[0493] Synthesis Example 2-12: Preparation of Compound 2-12

[0494]

[0495] Under a nitrogen atmosphere, intermediate 2-12-1 (10 g, 23.8 mmol) and intermediate 2-12-2 (8.8 g, 26.1 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.1 g, 95 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.4 g of compound 2-12.

[0496] (yield 69%, MS: [M+H] + =635)

[0497] Synthesis Example 2-13: Preparation of Compound 2-13

[0498]

[0499] Under a nitrogen atmosphere, intermediate 2-13-1 (10 g, 24.3 mmol) and intermediate 2-13-2 (11.1 g, 26.8 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9 g of compound 2-13.

[0500] (yield 53%, MS: [M+H] + =701)

[0501] Synthesis Example 2-14: Preparation of Compound 2-14

[0502]

[0503] Under a nitrogen atmosphere, intermediate 2-14-1 (10 g, 24.3 mmol) and intermediate 2-14-2 (7.7 g, 26.8 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.9 g of compound 2-14.

[0504] (yield 64%, MS: [M+H] + =575)

[0505] Synthesis Example 2-15: Preparation of Compound 2-15

[0506]

[0507] Under a nitrogen atmosphere, intermediate 2-15-1 (10 g, 24.3 mmol) and intermediate 2-15-2 (9 g, 26.8 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.4 g of compound 2-15.

[0508] (yield 55%, MS: [M+H] + =625)

[0509] Synthesis Example 2-16: Preparation of Compound 2-16

[0510]

[0511] Under a nitrogen atmosphere, intermediate 2-16-1 (10 g, 24.3 mmol) and intermediate 2-16-2 (11.1 g, 26.8 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 2-16.

[0512] (yield 66%, MS: [M+H] + =701)

[0513] Synthesis Example 2-17: Preparation of Compound 2-17

[0514]

[0515] Under a nitrogen atmosphere, intermediate 2-17-1 (10 g, 24.3 mmol) and intermediate 2-17-2 (10.1 g, 26.8 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10 g of compound 2-17.

[0516] (yield 62%, MS: [M+H] + =665)

[0517] Synthesis Example 2-18: Preparation of Compound 2-18

[0518]

[0519] Under a nitrogen atmosphere, intermediate 2-18-1 (10 g, 24.3 mmol) and intermediate 2-18-2 (10.5 g, 26.8 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 2-18.

[0520] (yield 59%, MS: [M+H] + =681)

[0521] Synthesis Example 2-19: Preparation of Compound 2-19

[0522]

[0523] Under a nitrogen atmosphere, intermediate 2-19-1 (10 g, 24.3 mmol) and intermediate 2-19-2 (10.5 g, 26.8 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 2-19.

[0524] (yield 69%, MS: [M+H] + =681)

[0525] Synthesis Example 2-20: Preparation of Compound 2-20

[0526]

[0527] Under a nitrogen atmosphere, intermediate 2-20-1 (10 g, 23.4 mmol) and intermediate 2-20-2 (9.4 g, 25.8 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (12.9 g, 93.7 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9 g of compound 2-20.

[0528] (yield 58%, MS: [M+H] + =667)

[0529] Synthesis Example 2-21: Preparation of Compound 2-21

[0530]

[0531] Under a nitrogen atmosphere, intermediate 2-21-1 (10 g, 23.4 mmol) and intermediate 2-21-2 (10.6 g, 25.8 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (12.9 g, 93.7 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, 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 2-21.

[0532] (yield 64%, MS: [M+H] + =717)

[0533] Synthesis Example 2-22: Preparation of Compound 2-22

[0534]

[0535] Under a nitrogen atmosphere, intermediate 2-22-1 (10 g, 23.4 mmol) and intermediate 2-22-2 (11.3 g, 25.8 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (12.9 g, 93.7 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9 g of compound 2-22.

[0536] (yield 52%, MS: [M+H] + =743)

[0537] Synthesis Example 2-23: Preparation of Compound 2-23

[0538]

[0539] Under a nitrogen atmosphere, intermediate 2-23-1 (10 g, 23.4 mmol) and intermediate 2-23-2 (10.1 g, 25.8 mmol) were added to 200 mL of THF and stirred. Potassium carbonate (12.9 g, 93.7 mmol) was dissolved in water and put into the mixture. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was put into the mixture during reflux. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The mixture was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.1 g of compound 2-23.

[0540] (yield 56%, MS: [M+H] + =697)

[0541] Example 1: Fabrication of an organic light-emitting device

[0542] ITO (indium tin oxide) The thickness of the glass substrate coated with a film is placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent uses Fischer Co. products, and the distilled water uses distilled water filtered twice by a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed and dried with a solvent of isopropyl alcohol, acetone, and methanol, and then the substrate is transported to a plasma cleaning machine. In addition, after the above-mentioned substrate is cleaned for 5 minutes, the substrate is transported to a vacuum deposition machine.

[0543] On the ITO transparent electrode prepared in this way, the following HI-1 compound was added as a hole injection layer. The following A-1 compound was p-doped at a concentration of 1.5%. On the hole injection layer, the following HT-1 compound was vacuum-deposited to form a film with a thickness of Then, on the hole transport layer, a film with a thickness of The electron suppression layer was formed by vacuum deposition of the following EB-1 compound.

[0544] Next, on the EB-1 vapor-deposited film, the compound 1 prepared in the above-mentioned synthesis example 1 as the first host, the compound 2-1 prepared in the above-mentioned synthesis example 2-1 as the second host, and the following Dp-7 compound as a dopant were vacuum-deposited to form In this case, the first host and the second host are used in a weight ratio of 1:1, and the total weight ratio of the host material and the dopant material is used in a weight ratio of 98:2.

[0545] On the above-mentioned light-emitting layer, the film thickness is The following HB-1 compound was vacuum-deposited to form a hole blocking layer. Next, the following ET-1 compound and the following LiQ compound were vacuum-deposited on the hole blocking layer at a weight ratio of 2:1, thereby forming a hole blocking layer. The electron injection and transport layer is formed with a thickness of The thickness of the aluminum A thickness of 1000 nm is evaporated to form a cathode.

[0546]

[0547] In the above process, the evaporation rate of organic matter is maintained at Lithium fluoride at the cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2×10 -7 ~5×10 -6 The organic light-emitting device is thus produced.

[0548] Example 2 to Example 100

[0549] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compounds listed in Tables 1 to 3 below were used as common host substances instead of Compound 1 and Compound 2-1.

[0550] Comparative Examples 1 to 37

[0551] In the organic light-emitting device of Example 1, an organic light-emitting device was manufactured by the same method as in Example 1, except that the single host compounds listed in Tables 4 and 5 below were used instead of Compound 1 and Compound 2-1 as the common host substances. The structures of Comparative Compounds C-1 to C-12 in Table 5 are shown below.

[0552]

[0553] Comparative Examples 38 to 85

[0554] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compounds described in Tables 6 and 7 below were used instead of Compound 1 and Compound 2-1 as the common host substances.

[0555] Experimental example

[0556] When current was applied to the organic light emitting devices prepared in Examples 1 to 100 and Comparative Examples 1 to 85, the current (15 mA / cm 2 The voltage, efficiency, and lifespan were measured (based on the reference voltage), and the results are shown in Tables 1 to 7. The lifespan T95 represents the time required for the luminance to decrease to 95% from the initial luminance (6000 nits).

[0557] [Table 1]

[0558]

[0559]

[0560] [Table 2]

[0561]

[0562]

[0563] [Table 3]

[0564]

[0565] [Table 4]

[0566] distinguish substance Efficiency (cd / A) Lifespan T95 (hr) Luminous color Comparative Example 1 Compound 1 20.3 122 red Comparative Example 2 Compound 3 21.1 135 red Comparative Example 3 Compound 5 23.2 148 red Comparative Example 4 Compound 9 22.6 127 red Comparative Example 5 Compound 10 21.8 143 red Comparative Example 6 Compound 14 23.2 157 red Comparative Example 7 Compound 17 22.6 145 red Comparative Example 8 Compound 19 21.4 128 red Comparative Example 9 Compound 21 23.5 172 red Comparative Example 10 Compound 23 19.4 126 red Comparative Example 11 Compound 25 20.2 129 red Comparative Example 12 Compound 29 21.3 141 red Comparative Example 13 Compound 30 21.5 133 red Comparative Example 14 Compound 31 20.2 145 red Comparative Example 15 Compound 32 21.6 157 red Comparative Example 16 Compound 33 22.3 140 red Comparative Example 17 Compound 34 21.6 152 red Comparative Example 18 Compound 35 22.2 143 red Comparative Example 19 Compound 36 22.8 142 red Comparative Example 20 Compound 37 21.6 158 red Comparative Example 21 Compound 38 22.3 141 red Comparative Example 22 Compound 39 21.5 151 red Comparative Example 23 Compound 40 20.7 160 red Comparative Example 24 Compound 41 22.6 159 red Comparative Example 25 Compound 42 23.4 163 red

[0567] [Table 5]

[0568] distinguish substance Efficiency (cd / A) Lifespan T95 (hr) Luminous color Comparative Example 26 C-1 17.4 107 red Comparative Example 27 C-2 16.1 83 red Comparative Example 28 C-3 16.4 94 red Comparative Example 29 C-4 16.0 87 red Comparative Example 30 C-5 18.7 110 red Comparative Example 31 C-6 16.8 51 red Comparative Example 32 C-7 15.5 24 red Comparative Example 33 C-8 15.1 37 red Comparative Example 34 C-9 17.3 75 red Comparative Example 35 C-10 17.5 92 red Comparative Example 36 C-11 15.8 63 red Comparative Example 37 C-12 16.1 78 red

[0569] [Table 6]

[0570]

[0571]

[0572] [Table 7]

[0573]

[0574] As shown in Tables 1 to 7 above, the organic light-emitting devices of the examples in which the first compound represented by Chemical Formula 1 and the second compound represented by Chemical Formula 2 are simultaneously used as host materials of the light-emitting layer exhibit excellent luminous efficiency and significantly improved lifespan characteristics compared to the organic light-emitting devices of the comparative examples in which only one of the compounds represented by Chemical Formulas 1 and 2 or neither is used.

[0575] Specifically, the device according to the embodiment shows high efficiency and long life compared with the device of the comparative example in which the compound represented by the above chemical formula 1 is used as a single host. In addition, the device according to the embodiment also improves the driving voltage, efficiency and life characteristics compared with the device of the comparative example in which the comparative example compounds C-1 to C-12 are used as the first host and the compound represented by the above chemical formula 2 is used as the second host. Thus, it is confirmed that when the combination of the first compound represented by the above chemical formula 1 and the second compound represented by the above chemical formula 2 is used as a common host, energy transfer to the red dopant is effectively achieved in the red light-emitting layer. It can be judged that this is because the first compound has high stability for electrons and holes. In addition, it is judged that because the second compound is used at the same time, the amount of holes increases, and at the same time, electrons and holes maintain a more stable balance in the red light-emitting layer.

[0576] Therefore, it was confirmed that the combined use of the first and second compounds as host materials in an organic light-emitting device can improve the driving voltage, luminous efficiency, and lifetime characteristics of the organic light-emitting device. Considering that luminous efficiency and lifetime characteristics of organic light-emitting devices generally exhibit a trade-off, it is believed that the organic light-emitting device using the combination of the compounds of the present invention exhibits significantly improved device characteristics compared to the comparative example device.

[0577] [Explanation of symbols]

[0578] 1: Substrate 2: Anode

[0579] 3: Light-emitting layer 4: Cathode

[0580] 5: Hole injection layer 6: Hole transport layer

[0581] 7: Electron suppression layer 8: Hole blocking layer

[0582] 9: Electron injection and transport layer.

Claims

1. An organic light-emitting device, comprising: anode; a cathode disposed opposite to the anode; as well as A light-emitting layer is provided between the anode and the cathode, The light-emitting layer comprises a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2': Chemical formula 1 In the chemical formula 1, X is O or S, L1 and L2 are each independently a single bond, or any one selected from the following groups, One of Ar1 and Ar2 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl or fluorenyl, and the other is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl, wherein Ar1 and Ar2 are unsubstituted or are selected from deuterium, C 1-10 The alkyl group and the phenyl group are substituted with one or more substituents, R is each independently hydrogen or deuterium, a is an integer from 1 to 3, b is an integer from 1 to 6, Chemical formula 2' In the chemical formula 2', B1 and B2 are each independently a benzene or naphthalene ring, L'1 and L'2 are each independently a single bond; or unsubstituted or deuterated C 6-20 arylene groups, Ar'1 and Ar'2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluoranthenyl, fluorenyl, 9,9'-spirobifluorenyl, dibenzofuranyl or dibenzothiophenyl, wherein Ar'1 and Ar'2 are unsubstituted or are selected from deuterium, C 1-10 The alkyl group and the phenyl group are substituted with one or more substituents, R' is each independently hydrogen or deuterium, and c and d are each independently an integer from 1 to 6, When a, b, c, and d are each 2 or more, the substituents in the brackets may be the same as or different from each other.

2. The organic light-emitting device according to claim 1, wherein L1 is a single bond, 3. The organic light-emitting device according to claim 1, wherein L2 is a single bond, or any one selected from the following groups: The organic light-emitting device according to claim 1 , wherein: Ar1 is phenyl, biphenyl or naphthyl, and Ar2 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, 9-phenylcarbazolyl or carbazolyl. The organic light-emitting device according to claim 1 , wherein: The first compound is represented by any one of the following chemical formulas 1-1-1 to 1-1-3: In the chemical formulas 1-1-1 to 1-1-3, X, L2, Ar1 and Ar2 are the same as defined in claim 1. The organic light-emitting device according to claim 1 , wherein: The first compound is any one selected from the following compounds:

7. The organic light-emitting device according to claim 1, wherein B1 and B2 are benzene rings.

8. The organic light-emitting device according to claim 1, wherein L'1 and L'2 are each independently a single bond, an unsubstituted or deuterium-substituted phenylene group, or an unsubstituted or deuterium-substituted naphthylene group.

9. The organic light emitting device according to claim 1, wherein Ar'1 and Ar'2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluoranthenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirobifluorenyl, dibenzofuranyl or dibenzothiophenyl.

10. The organic light emitting device according to claim 1, wherein The second compound is represented by the following chemical formula 2-1: Chemical formula 2-1 In the chemical formula 2-1, L'1, L'2, Ar'1, and Ar'2 are the same as defined in claim 1. The organic light-emitting device according to claim 1 , wherein: The second compound is any one selected from the following compounds:

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