Novel compounds and organic light-emitting devices comprising the same

Abstract

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

Description

Technical Field

[0001] Cross-reference with related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2020-0106501 dated August 24, 2020 and Korean Patent Application No. 10-2021-0111730 dated August 24, 2021, the entire contents of which are disclosed in the documents of the Korean patent applications and are incorporated herein by reference.

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

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

[0005] Organic light-emitting devices (OLEDs) typically have a structure comprising an anode and a cathode, and an organic layer located between the anode and cathode. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, they form excitons, which emit light when they re-enter the ground state.

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

[0007] Existing technical documents

[0008] Patent documents

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

[0010] Technical issues

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

[0012] Solution to the problem

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

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] A and B are each independently benzene rings fused with adjacent rings.

[0018] n1 and n2 are each independently 0 or 1.

[0019] Ar1 represents substituted or unsubstituted C. 6-60 Aryl,

[0020] L1 represents a single bond, or a substituted or unsubstituted C bond. 6-60 Alpha-aryl

[0021] R1 can be either hydrogen or deuterium independently.

[0022] R2 atoms can be hydrogen or deuterium independently; or they can combine with each other to form a benzene ring.

[0023] One of R3 is a substituent represented by the following chemical formula 2, and the rest are hydrogen or deuterium.

[0024] [Chemical Formula 2]

[0025]

[0026] In the above chemical formula 2,

[0027] L2 is a single bond, or a substituted or unsubstituted C bond. 6-60 Alpha-aryl

[0028] Ar2 is C with or without substitution. 6-20 aryl; or substituted or unsubstituted C containing one or more of N, O, and S. 2-20 Mixed aromatics,

[0029] Ar3 is a substituent represented by the following chemical formula 3.

[0030] [Chemical Formula 3]

[0031]

[0032] In the above chemical formula 3,

[0033] X is O or S.

[0034] R4 atoms are either hydrogen or deuterium; or two adjacent atoms may combine to form a benzene ring, with the remainder being hydrogen or deuterium.

[0035] R5 atoms are individually hydrogen or deuterium; or two adjacent atoms may combine to form a benzene ring, with the remainder being hydrogen or deuterium.

[0036] However, at least one pair of R4 or at least one pair of adjacent R5 molecules must bond to form a benzene ring.

[0037] m1 is an integer from 1 to 3.

[0038] m2 is an integer from 1 to 4.

[0039] But Ar3 is not .

[0040] In addition, the present invention provides an organic light-emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the above chemical formula 1.

[0041] Invention Effects

[0042] The compounds represented by the above-described chemical formula 1 can be used as materials for the organic layer of organic light-emitting devices, thereby achieving improved efficiency, lower driving voltage, and / or improved lifetime characteristics in organic light-emitting devices. In particular, the compounds represented by the above-described chemical formula 1 are suitable for solution processing and can be used as materials for hole injection, hole transport, hole injection and transport, electron suppression, luminescence, hole blocking, electron transport, electron injection, or electron injection and transport. Attached Figure Description

[0043] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

[0044] Figure 2 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. Detailed Implementation

[0045] The invention will now be described in more detail to aid in understanding.

[0046] In this instruction manual, or This indicates a bond that is linked to other substituents.

[0047] In this specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thio group ( ); aryl thio ( ); alkylsulfonyl ( ); arylsulfonyl ( ); silyl; boronyl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; arylene; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphinyl; or a substituent formed by connecting two or more of the substituents exemplified above, whether substituted or unsubstituted. For example, "a substituent formed by connecting two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent formed by connecting two phenyl groups.

[0048] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferred to have 1 to 40 carbon atoms. Specifically, it can be a group with the following structure, but is not limited thereto.

[0049]

[0050] In this specification, the oxygen atom in the ester group may be replaced by a straight-chain, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a group with the following structural formula, but is not limited thereto.

[0051]

[0052] In this specification, the number of carbon atoms in the imide group is not particularly limited, but it is preferred to have 1 to 25 carbon atoms. Specifically, it can be a group with the following structure, but is not limited thereto.

[0053]

[0054] In this specification, silanes specifically include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited to these.

[0055] In this specification, the boron group specifically includes trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but is not limited to these.

[0056] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0057] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0058] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc., but are not limited to these.

[0059] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0060] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, thionyl, fluoreneyl, etc., but is not limited to these.

[0061] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure. When the fluorene group is substituted as described above, it can become... Etc. But it is not limited to this.

[0062] In this specification, a heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as heteroelements. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazole, and thiazolyl. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, iso Azolyl, thiadiazolyl, phenthiazinyl, and dibenzofuranyl groups, but not limited to these.

[0063] In this specification, the aryl groups in aralkyl, aryl-alkenyl, alkylaryl, and arylamine are the same as those exemplified above. In this specification, the alkyl groups in aralkyl, alkylaryl, and alkylamine are the same as those exemplified above. In this specification, the heteroaryl groups in heteroarylamines are subject to the above description of heterocyclic groups. In this specification, the alkenyl groups in aryl-alkenyl are the same as those exemplified above. In this specification, arylene is a divalent group; otherwise, the above description of aryl groups applies. In this specification, heteroarylene is a divalent group; otherwise, the above description of heterocyclic groups applies. In this specification, the hydrocarbon ring is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of aryl or cycloalkyl groups applies. In this specification, the heterocycle is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of heterocyclic groups applies.

[0064] The present invention provides compounds represented by the above chemical formula 1.

[0065] Specifically, the compound represented by the above-mentioned chemical formula 1 is a compound in which a tertiary amine group of benzo[a]naphthofuranyl or benzo[a]naphthothiophene group is attached to a specific position of the core structure of a carbazole-based polycyclic ring, together with a specific aryl or heteroaryl group. The compound is characterized in that no substituents other than the aforementioned tertiary amine and hydrogen or deuterium are attached to the core of the carbazole-based polycyclic ring. In particular, compared with compounds in which other aryl or heteroaryl groups such as triazine are substituted at the substitution position of the tertiary amine group attached to the benzo[a]naphthofuranyl or benzo[a]naphthothiophene group, the above-mentioned compound can effectively transport holes to the dopant material, and therefore can be effectively used in the light-emitting layer or hole transport layer of organic light-emitting devices.

[0066] Specifically, in the above chemical formula 1,

[0067] A and B are each independently benzene rings fused with adjacent rings.

[0068] n1 and n2 are each independently 0 or 1.

[0069] Ar1 represents substituted or unsubstituted C. 6-60 Aryl,

[0070] L1 represents a single bond, or a substituted or unsubstituted C bond. 6-60 Alpha-aryl

[0071] R1 can be either hydrogen or deuterium independently.

[0072] R2 atoms can be hydrogen or deuterium independently; or they can combine with each other to form a benzene ring.

[0073] One of R3 is a substituent represented by the following chemical formula 2, and the rest are hydrogen or deuterium.

[0074] [Chemical Formula 2]

[0075]

[0076] In the above chemical formula 2,

[0077] L2 is a single bond, or a substituted or unsubstituted C bond. 6-60 Alpha-aryl

[0078] Ar2 is C with or without substitution. 6-20 aryl; or substituted or unsubstituted C containing one or more of N, O, and S. 2-15 Mixed aromatics,

[0079] Ar3 is a substituent represented by the following chemical formula 3.

[0080] [Chemical Formula 3]

[0081]

[0082] In the above chemical formula 3,

[0083] X is O or S.

[0084] R4 atoms are either hydrogen or deuterium; or two adjacent atoms may combine to form a benzene ring, with the remainder being hydrogen or deuterium.

[0085] R5 atoms are individually hydrogen or deuterium; or two adjacent atoms may combine to form a benzene ring, with the remainder being hydrogen or deuterium.

[0086] However, at least one pair of R4 or at least one pair of adjacent R5 molecules must bond to form a benzene ring.

[0087] m1 is an integer from 1 to 3.

[0088] m2 can be an integer from 1 to 4.

[0089] But Ar3 is not .

[0090] Specifically, the above chemical formula 1 is represented by any one of the above chemical formulas 1-1 to 1-41:

[0091]

[0092]

[0093]

[0094] In the above chemical formulas 1-1 to 1-41, Ar1, L1 and R3 are defined in the same way as in chemical formula 1.

[0095] In this invention, chemical formula 1 is preferably chemical formula 1-1, chemical formula 1-2, chemical formula 1-3, chemical formula 1-4, chemical formula 1-5, chemical formula 1-6, chemical formula 1-7, chemical formula 1-8, chemical formula 1-9, chemical formula 1-10, chemical formula 1-11, chemical formula 1-12, chemical formula 1-13, chemical formula 1-14, chemical formula 1-15, chemical formula 1-16, chemical formula 1-18, chemical formula 1-20, chemical formula 1-33, chemical formula 1-34, chemical formula 1-35, chemical formula 1-36, chemical formula 1-37, chemical formula 1-38, chemical formula 1-39, chemical formula 1-40, or chemical formula 1-41.

[0096] More preferably, in this invention, chemical formula 1 can be chemical formula 1-2, chemical formula 1-3, chemical formula 1-4, chemical formula 1-6, chemical formula 1-10, chemical formula 1-14, chemical formula 1-34, chemical formula 1-38, or chemical formula 1-41.

[0097] On the other hand, in the above chemical formula 1, n1 and n2 are both 0; or one of n1 and n2 is 1, and the others are 0.

[0098] In addition, in the above chemical formula 1, A and B can each be a benzene ring fused with an adjacent ring; or either A or B can be a benzene ring fused with an adjacent ring.

[0099] Furthermore, n1 and n2 can each be 0 or 1, and at least one of n1 and n2 can be 1. Preferably, one of n1 and n2 can be 1 and the rest can be 0; or both n1 and n2 can be 0.

[0100] Specifically, in the above chemical formulas 1 and 1-1 to 1-20, L1 can be a single bond; or a substituted or unsubstituted C. 6-30 aryl, or C 6-28 aryl, or C 6-25 aryl, or C 6-20 Alpha-aryl.

[0101] As an example, L1 can be a single bond, or it can be represented by any of the groups selected from the following groups.

[0102]

[0103] Preferably, L1 is a single bond or a phenylene group; more preferably, L1 is a single bond.

[0104] In addition, in the above chemical formulas 1 and 1-1 to 1-20, Ar1 is phenyl, biphenyl, or naphthyl.

[0105] More specifically, Ar1 can be selected from any of the following groups, but is not limited to them:

[0106]

[0107] On the other hand, in formula 2, which relates to the amine group attached to the carbazole group of formula 1 above, L2 can be a single bond; or a substituted or unsubstituted C. 6-30 aryl, or C 6-28 aryl, or C 6-25 aryl, or C 6-20 Alpha-aryl.

[0108] Specifically, L2 is a single bond; or a phenylene, biphenylene, terphenylene, tetraphenylene, or naphthylene.

[0109] As an example, L2 can be a single bond, or it can be represented by any of the groups selected from the following groups.

[0110]

[0111] Furthermore, in the above chemical formula 2, Ar2 can be a substituted or unsubstituted C. 6-20 aryl; or substituted or unsubstituted C 6-18 aryl; or substituted or unsubstituted C containing one or more of N, O, and S. 2-15 heteroaryl, C 3-15 heteroaryl, or C 5-15 heteroaryl, or C 6-15 heteroaryl, or C 8-12 Mixed aromatic compounds.

[0112] Here, the Ar2 mentioned above may contain one of O or S, or may not contain any heteroatoms at all. In particular, Ar2 may be substituted or unsubstituted C. 6-18 aryl; or substituted or unsubstituted C containing O or S. 6-15 heteroaryl, or C 8-12 Mixed aromatic compounds.

[0113] Preferably, Ar2 is phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, naphthyl, phenanthryl, phenyl-substituted naphthyl, naphthyl-substituted naphthyl, phenyl-substituted phenanthryl, triphenylene, dibenzofuranyl, or dibenzothiopheneyl.

[0114] As an example, Ar2 can be any one of the following groups.

[0115]

[0116] On the other hand, in formula 3, which relates to the heterocycles attached to the amine groups of the above-mentioned formula 2, two adjacent R4 groups are attached to form a benzene ring, or two adjacent R5 groups are attached to form a benzene ring, with the remainder in R4 and R5 being hydrogen or deuterium.

[0117] As an example, in the compounds of the present invention, preferably, the above chemical formula 3 is represented by any one of the following chemical formulas 3-1 to 3-6, depending on the position of the benzene ring formed by the two adjacent bonds in R4 or R5.

[0118]

[0119] In the above chemical formulas 3-1 to 3-6, X has the same definition as in chemical formula 1.

[0120] But Ar3 is not .

[0121] More specifically, in the above chemical formula 1, Ar3 can be any one of the following groups.

[0122] .

[0123] Representative examples of compounds represented by the above chemical formula 1 are shown below.

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] On the other hand, the compound represented by the above chemical formula 1 can be manufactured by the manufacturing method shown in reaction formula 1 below. The above manufacturing method can be further specified in the synthesis examples described later.

[0178] [Reaction Formula 1]

[0179]

[0180] In the above reaction formula 1, A, B, n1, n2, R1, R2, R3, L1, L2, Ar1, Ar2, and Ar3 are the same as defined in the above chemical formula 1.

[0181] One of X1 is a halogen, and the rest are hydrogen or deuterium. In particular, one of X1 is preferably Cl, Br or I.

[0182] X2 is a halogen, and in particular, a halogen that is different from X1. Preferably, X2 is Cl, Br, or I.

[0183] As an example, one of X1 is Br or I, more preferably Br, and the remainder of X1 is hydrogen or deuterium. As an example, X2 is Cl or Br, more preferably Cl.

[0184] Specifically, reaction formula 1 described above is as follows: for a carbazole-based polycyclic core structure, a primary amine compound containing a specific aryl or heteroaryl group is reacted to generate a secondary amine group, and then a specific benzo[a]naphthofuran or benzo[a]naphthothiophene group is introduced into the secondary amine group, thereby introducing a specific tertiary amine group at a specific position in the carbazole-based polycyclic core structure. Specifically, in reaction formula 1, the secondary amine group generation reaction and the introduction of the benzo[a]naphthofuran or benzo[a]naphthothiophene group into the secondary amine group are carried out in the presence of a base using a palladium catalyst (Pd catalyst). The specific reaction conditions for such reaction formula 1 can be implemented with reference to reactions known in the art. The above manufacturing method can be further specified in the synthetic examples described later.

[0185] Furthermore, in the above reaction formula 1, the base component can be sodium tert-butoxide (NaOtBu), potassium carbonate (K2CO3), sodium bicarbonate (NaHCO3), cesium carbonate (Cs2CO3), sodium acetate (NaOAc), potassium acetate (KOAc), sodium ethoxide (NaOEt), or triethylamine (Et3N), N,N-diisopropylethylamine (EtN(iPr)2), etc. Preferably, the base component can be sodium tert-butoxide (NaOtBu), potassium carbonate (K2CO3), cesium carbonate (Cs2CO3), potassium acetate (KOAc), or N,N-diisopropylethylamine (EtN(iPr)2). More preferably, the base component can be sodium tert-butoxide (NaOtBu).

[0186] Additionally, in reaction formula 1 above, the palladium catalysts used can be bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu3)2, tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4, tris(dibenzylideneacetone)dipalladium(0), and bis(dibenzylideneacetone)palladium(0). The palladium catalyst can be bis(dibenzylideneacetone)palladium(O), Pd(dba)2, or palladium(II)acetate, Pd(OAc)2, etc. Preferably, the palladium catalyst can be bis(tris(tert-butylphosphine)palladium(O) (Pd(P-tBu3)2), tetra(triphenylphosphine)palladium(O) (Pd(PPh3)4), or bis(dibenzylideneacetone)palladium(O) (Pd(dba)2). In particular, in the above reaction formula 1, bis(tris(tert-butylphosphine)palladium(O) (Pd(P-tBu3)2) can be used as the catalyst.

[0187] In this specification, equivalent (eq.) refers to molar equivalent.

[0188] On the other hand, the present invention provides an organic light-emitting device comprising a compound represented by the above-described chemical formula 1. As an example, the present invention provides an organic light-emitting device comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the above-described chemical formula 1.

[0189] The organic layer of the organic light-emitting device of the present invention can be formed as a single-layer structure, or it can be formed as a multi-layer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of the present invention can have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer as organic layers. However, the structure of the organic light-emitting device is not limited to this, and may include fewer organic layers.

[0190] In addition, the aforementioned organic layer may include a hole injection layer, a hole transport layer, or a layer that performs both hole injection and transport simultaneously, wherein the aforementioned hole injection layer, hole transport layer, or layer that performs both hole injection and transport simultaneously comprises a compound represented by the aforementioned chemical formula 1.

[0191] In addition, the aforementioned organic layer may include an electron suppression layer comprising a compound represented by the aforementioned chemical formula 1.

[0192] In addition, the aforementioned organic layer may include a light-emitting layer, which contains a compound represented by the aforementioned chemical formula 1.

[0193] In addition, the aforementioned light-emitting layer also contains dopant compounds.

[0194] In addition, the above-mentioned light-emitting layer contains a compound of chemical formula 1 and a dopant.

[0195] As an example, the light-emitting layer described above contains a compound of chemical formula 1 and a dopant, and contains the compound of chemical formula 1 and the dopant in a content ratio of 100:1 to 1:1.

[0196] In addition, the light-emitting layer contains a compound of chemical formula 1 and a dopant, and contains the compound of chemical formula 1 and the dopant in a content ratio of 100:1 to 2:1.

[0197] In addition, the light-emitting layer contains a compound of chemical formula 1 and a dopant, and contains the compound of chemical formula 1 and the dopant in a content ratio of 100:1 to 5:1.

[0198] As an example, the dopant mentioned above is a metal complex.

[0199] Specifically, the dopant mentioned above is an iridium-based metal complex.

[0200] In addition, the organic layer mentioned above includes a light-emitting layer, which contains a dopant, and the dopant material is selected from the following structural formula.

[0201]

[0202]

[0203]

[0204] .

[0205] The structures described above are dopant compounds, but are not limited to them.

[0206] In addition, the aforementioned organic layer may include a hole-blocking layer comprising a compound represented by the aforementioned chemical formula 1.

[0207] In addition, the aforementioned organic layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron injection and transport, wherein the aforementioned electron transport layer, electron injection layer, or layer that simultaneously performs electron injection and transport contains a compound represented by the aforementioned chemical formula 1.

[0208] In addition, the aforementioned organic layer includes a light-emitting layer and a hole transport layer, and the light-emitting layer or hole transport layer may contain a compound represented by the aforementioned chemical formula 1.

[0209] Furthermore, the organic light-emitting device according to the present invention can be a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. Additionally, the organic light-emitting device according to the present invention can be a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated below. Figure 1 and 2 .

[0210] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 may be included in the light-emitting layer.

[0211] Figure 2The illustration shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. In the structure described above, the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, hole transport layer, electron suppression layer, light-emitting layer, hole blocking layer, and electron injection and transport layer. Specifically, the compound represented by Chemical Formula 1 may be included as a material for the electron suppression layer.

[0212] The organic light-emitting device according to the present invention, except that one or more of the organic layers contain a compound represented by the above-described chemical formula 1, can be manufactured using materials and methods known in the art. Furthermore, when the organic light-emitting device comprises a plurality of organic layers, the organic layers can be formed from the same substance or different substances.

[0213] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; then forming an organic layer on the anode, comprising a hole injection layer, a hole transport layer, an electron suppression layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; and finally depositing a material suitable for use as a cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0214] Furthermore, the compound represented by the above chemical formula 1 can be used to form organic layers in the manufacture of organic light-emitting devices not only by vacuum evaporation but also by solution coating. In particular, the compound represented by the above chemical formula 1 has excellent solubility in the solvents used in solution coating, thus making it easy to apply solution coating methods. Here, solution coating methods refer to, but are not limited to, spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roll coating.

[0215] Therefore, the present invention provides a coating composition comprising a compound represented by the above chemical formula 1 and a solvent.

[0216] The solvents mentioned above are not particularly limited as long as they can dissolve or disperse the compounds according to the present invention. Examples include chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, and other chlorinated solvents; tetrahydrofuran, dichloromethane, dichlorobenzene, etc. Ether solvents such as alkanes; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, and diethoxyethane. Polyols such as methane, triethylene glycol monoethyl ether, glycerol, and 1,2-hexanediol and their derivatives; alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as butyl benzoate and methyl 2-methoxybenzoate; tetrahydronaphthalene; and 3-phenoxy-toluene. Furthermore, one of the above-mentioned solvents can be used alone or in combination with two or more solvents.

[0217] Furthermore, the viscosity of the above-described coating composition is preferably from 1 cP to 10 cP, within which it is easily applied. Additionally, the concentration of the compound according to the invention in the above-described coating composition is preferably from 0.1 wt / v% to 20 wt / v.

[0218] Furthermore, the present invention provides a method for forming a functional layer using the above-described coating composition. Specifically, it includes a step of coating the coating composition according to the present invention using a solution process, and a step of heat-treating the coated coating composition.

[0219] In the above heat treatment step, the heat treatment temperature is preferably between 150°C and 230°C. Furthermore, the heat treatment time is between 1 minute and 3 hours, more preferably between 10 minutes and 1 hour. Additionally, the heat treatment is preferably performed in an atmosphere of inert gas such as argon or nitrogen.

[0220] As an example, the first electrode is the anode and the second electrode is the cathode, or the first electrode is the cathode and the second electrode is the anode.

[0221] As the aforementioned anode material, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. Specific examples of the aforementioned anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0222] As the cathode material described above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0223] The aforementioned hole injection layer is a layer that injects holes from the electrode. Preferably, the hole injection material is a compound that possesses the ability to transport holes, the effect of injecting holes from the anode, excellent hole injection performance for the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and exhibits excellent thin film formation capability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between that of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene.

[0224] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a material capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; materials with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers that simultaneously contain conjugated and non-conjugated portions, but are not limited to these.

[0225] The aforementioned luminescent materials are those capable of receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining them to emit light in the visible light region. Preferably, these materials possess high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole compounds; diluted styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds including azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0226] The aforementioned luminescent layer may comprise a host material and a dopant material. The host material may be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but are not limited to these. Preferably, the compound according to the present invention is used as the aforementioned host material.

[0227] As dopant materials, there are aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives having substituted or unsubstituted aryl amino groups, such as pyrene, anthracene, benzo[a]pyrene, etc., having aryl amino groups. Styrene amine compounds are compounds in which at least one aryl vinyl group is substituted on a substituted or unsubstituted aryl amine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrene amines, styrene diamines, styrene triamines, styrene tetraamines, etc., but they are not limited to these. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these. Preferably, iridium-based metal complexes are used as the above-mentioned dopant materials.

[0228] The aforementioned light-emitting layer can be a red light-emitting layer. When the compound according to the present invention is used as the host material, the stability of electrons and holes becomes higher, and the energy transfer from the host to the red dopant is well formed, thereby improving the driving voltage, luminous efficiency and lifetime characteristics of the organic light-emitting device.

[0229] The aforementioned electron transport layer is the layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is one that can effectively receive electrons from the cathode and transfer them to the light-emitting layer; materials with high electron mobility are suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common materials with low work functions and accompanied by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium are all accompanied by an aluminum or silver layer.

[0230] The aforementioned electron injection layer is a layer that injects electrons from the electrode. Preferably, it is a compound that possesses the ability to transport electrons, the effect of injecting electrons from the cathode, excellent electron injection effect for the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the hole injection layer, and has excellent thin film forming ability. Specifically, it includes fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0231] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0232] The organic light-emitting device according to the present invention can be a bottom-emission device, a top-emission device, or a bidirectional light-emitting device, and in particular, it can be a bottom-emission device that requires relatively high luminous efficiency.

[0233] In addition, the compounds according to the present invention can be included not only in organic light-emitting devices, but also in organic solar cells or organic transistors.

[0234] The manufacture of compounds represented by the above chemical formula 1 and organic light-emitting devices containing them is specifically described in the following examples. However, the following examples are for illustrative purposes only and the scope of the invention is not limited thereto.

[0235] [Example]

[0236] Synthesis Example 1. Synthesis of Compound 1

[0237]

[0238] Under a nitrogen atmosphere, compound sub1 (10 g, 31 mmol), amine 1 (8 g, 32.6 mmol), and sodium tert-butoxide (NaOtBu, 3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (Pd(t-Bu3P)2, 15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 10.4 g of compound sub1-1. (Yield 69%, MS: [M+H)) + =487).

[0239] Under a nitrogen atmosphere, compound 1-1 (10 g, 20.5 mmol), compound A (5.5 g, 21.6 mmol), and sodium tert-butoxide (2.6 g, 26.7 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (10.5 g, 20.5 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 7.5 g of compound 1. (Yield 52%, MS: [M+H)) + =703).

[0240] Synthesis Example 2. Synthesis of Compound 2

[0241]

[0242] Under a nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 2 (5.5 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 6.9 g of compounds 1-2. (Yield 54%, MS: [M+H)) + =411).

[0243] Under a nitrogen atmosphere, compounds 1-2 (10 g, 24.4 mmol), compound B (6.5 g, 25.6 mmol), and sodium tert-butoxide (3 g, 31.7 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (12.4 g, 24.4 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to give 10.7 g of compound 2. (Yield 70%, MS: [M+H)) + =627).

[0244] Synthesis Example 3. Synthesis of Compound 3

[0245]

[0246] Under a nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 3 (8.8 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 10.1 g of compounds 1-3. (Yield 64%, MS: [M+H)) + =511).

[0247] Under a nitrogen atmosphere, compounds 1-3 (10 g, 19.6 mmol), compound B (5.2 g, 20.6 mmol), and sodium tert-butoxide (2.4 g, 25.5 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (10 g, 19.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to give 9 g of compound 3. (Yield 63%, MS: [M+H)) + =727).

[0248] Synthesis Example 4. Synthesis of Compound 4

[0249]

[0250] Under a nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 4 (8 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 7.5 g of compounds 1-4. (Yield 50%, MS: [M+H)) + =487).

[0251] Under a nitrogen atmosphere, compounds 1-4 (10 g, 23.4 mmol), compound C (6.2 g, 24.6 mmol), and sodium tert-butoxide (2.9 g, 30.5 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (12 g, 23.4 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to give 8.4 g of compound 4. (Yield 51%, MS: [M+H]) + =704).

[0252] Synthesis Example 5. Synthesis of Compound 5

[0253]

[0254] Under a nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 5 (6.5 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 8.7 g of compounds 1-5. (Yield 64%, MS: [M+H)) + =441).

[0255] Under a nitrogen atmosphere, compounds 1-5 (10 g, 22.7 mmol), compound D (6 g, 23.8 mmol), and sodium tert-butoxide (2.8 g, 29.5 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (11.6 g, 22.7 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to give 9.1 g of compound 5. (Yield 61%, MS: [M+H)) + =658).

[0256] Synthesis Example 6. Synthesis of Compound 6

[0257]

[0258] Under a nitrogen atmosphere, compound 2 (10 g, 26.9 mmol), compound amine 6 (4.8 g, 28.2 mmol), and sodium tert-butoxide (3.4 g, 34.9 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (13.7 g, 26.9 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7 g of compound 2-1. (Yield 57%, MS: [M+H)) + =461).

[0259] Under a nitrogen atmosphere, compound 2-1 (10 g, 21.7 mmol), compound E (5.8 g, 22.8 mmol), and sodium tert-butoxide (2.7 g, 28.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (11.1 g, 21.7 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.8 g of compound 6. (Yield 67%, MS: [M+H)) + =677).

[0260] Synthesis Example 7. Synthesis of Compound 7

[0261]

[0262] Under a nitrogen atmosphere, compound 2 (10 g, 26.9 mmol), compound amine 7 (7.6 g, 28.2 mmol), and sodium tert-butoxide (3.4 g, 34.9 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (13.7 g, 26.9 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.7 g of compound 2-2. (Yield 51%, MS: [M+H]) + =561).

[0263] Under a nitrogen atmosphere, compound 2-2 (10 g, 17.8 mmol), compound F (4.7 g, 18.7 mmol), and sodium tert-butoxide (2.2 g, 23.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (9.1 g, 17.8 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8 g of compound 7. (Yield 58%, MS: [M+H)) + =777).

[0264] Synthesis Example 8. Synthesis of Compound 8

[0265]

[0266] Under a nitrogen atmosphere, compound 2 (10 g, 26.9 mmol), compound amine 8 (6.9 g, 28.2 mmol), and sodium tert-butoxide (3.4 g, 34.9 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (13.7 g, 26.9 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 9.7 g of compounds 2-3. (Yield 67%, MS: [M+H)) + =537).

[0267] Under a nitrogen atmosphere, compounds 2-3 (10 g, 18.6 mmol), compound G (4.9 g, 19.6 mmol), and sodium tert-butoxide (2.3 g, 24.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (9.5 g, 18.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to give 7.7 g of compound 8. (Yield 55%, MS: [M+H)) + =753).

[0268] Synthesis Example 9. Synthesis of Compound 9

[0269]

[0270] Under a nitrogen atmosphere, compound 3 (10 g, 25.1 mmol), compound amine 9 (7.8 g, 26.4 mmol), and sodium tert-butoxide (3.1 g, 32.6 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (12.8 g, 25.1 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 3-1. (Yield 61%, MS: [M+H)) + =613).

[0271] Under a nitrogen atmosphere, compound 3-1 (10 g, 16.3 mmol), compound H (4.3 g, 17.1 mmol), and sodium tert-butoxide (2 g, 21.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (8.3 g, 16.3 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 7.4 g of compound 9. (Yield 55%, MS: [M+H)) + =829).

[0272] Synthesis Example 10. Synthesis of Compound 10

[0273]

[0274] Under a nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 10 (7.1 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.1 g of compound 4-1. (Yield 64%, MS: [M+H)) + =461).

[0275] Under a nitrogen atmosphere, compound 4-1 (10 g, 21.7 mmol), compound B (5.8 g, 22.8 mmol), and sodium tert-butoxide (2.7 g, 28.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (11.1 g, 21.7 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8.2 g of compound 10. (Yield 56%, MS: [M+H]) + =677).

[0276] Synthesis Example 11. Synthesis of Compound 11

[0277]

[0278] Under a nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 11 (9.6 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.8 g of compound 4-2. (Yield 59%, MS: [M+H]) + =537).

[0279] Under a nitrogen atmosphere, compound 4-2 (10 g, 18.6 mmol), compound I (4.9 g, 19.6 mmol), and sodium tert-butoxide (2.3 g, 24.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (9.5 g, 18.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 7.1 g of compound 11. (Yield 51%, MS: [M+H)) + =753).

[0280] Synthesis Example 12. Synthesis of Compound 12

[0281]

[0282] Under a nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 12 (6 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of compound 4-3. (Yield 60%, MS: [M+H)) + =425).

[0283] Under a nitrogen atmosphere, compound 4-3 (10 g, 23.6 mmol), compound G (6.3 g, 24.7 mmol), and sodium tert-butoxide (2.9 g, 30.6 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (12 g, 23.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.2 g of compound 12. (Yield 61%, MS: [M+H)) + =641).

[0284] Synthesis Example 13. Synthesis of Compound 13

[0285]

[0286] Under a nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 13 (6.3 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.7 g of compound 4-4. (Yield 50%, MS: [M+H)) + =435).

[0287] Under a nitrogen atmosphere, compound 4-4 (10 g, 23 mmol), compound J (6.1 g, 24.2 mmol), and sodium tert-butoxide (2.9 g, 29.9 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (11.8 g, 23 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.1 g of compound 13. (Yield 61%, MS: [M+H)) + =651).

[0288] Synthesis Example 14. Synthesis of Compound 14

[0289]

[0290] Under a nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 14 (8 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 8.6 g of compounds 4-5. (Yield 57%, MS: [M+H)) + =487).

[0291] Under a nitrogen atmosphere, compounds 4-5 (10 g, 20.5 mmol), compound H (5.5 g, 21.6 mmol), and sodium tert-butoxide (2.6 g, 26.7 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (10.5 g, 20.5 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.4 g of compound 14. (Yield 65%, MS: [M+H]) + =703).

[0292] Synthesis Example 15. Synthesis of Compound 15

[0293]

[0294] Under a nitrogen atmosphere, compound 5 (10 g, 26.9 mmol), compound amine 15 (6.2 g, 28.2 mmol), and sodium tert-butoxide (3.4 g, 34.9 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (13.7 g, 26.9 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8.2 g of compound 5-1. (Yield 60%, MS: [M+H)) + =511).

[0295] Under a nitrogen atmosphere, compound 5-1 (10 g, 19.6 mmol), compound B (5.2 g, 20.6 mmol), and sodium tert-butoxide (2.4 g, 25.5 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (10 g, 19.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 7.3 g of compound 15. (Yield 51%, MS: [M+H)) + =727).

[0296] Synthesis Example 16. Synthesis of Compound 16

[0297]

[0298] Under a nitrogen atmosphere, compound 6 (10 g, 31 mmol), compound amine 16 (9.6 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.3 g of compound 6-1. (Yield 62%, MS: [M+H)) + =537).

[0299] Under a nitrogen atmosphere, compound 6-1 (10 g, 18.6 mmol), compound J (4.9 g, 19.6 mmol), and sodium tert-butoxide (2.3 g, 24.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (9.5 g, 18.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 7.1 g of compound 16. (Yield 51%, MS: [M+H)) + =753).

[0300] Synthesis Example 17. Synthesis of Compound 17

[0301]

[0302] Under a nitrogen atmosphere, compound 7 (10 g, 31 mmol), compound amine 17 (3 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of compound 7-1. (Yield 66%, MS: [M+H)) + =385).

[0303] Under a nitrogen atmosphere, compound 7-1 (10 g, 26 mmol), compound I (6.9 g, 27.3 mmol), and sodium tert-butoxide (3.2 g, 33.8 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (13.3 g, 26 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.8 g of compound 17. (Yield 63%, MS: [M+H)) + =601).

[0304] Synthesis Example 18. Synthesis of Compound 18

[0305]

[0306] Under a nitrogen atmosphere, compound 8 (10 g, 31 mmol), compound amine 7 (8.8 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.3 g of compound 8-1. (Yield 59%, MS: [M+H)) + =561).

[0307] Under a nitrogen atmosphere, compound 8-1 (10 g, 17.8 mmol), compound G (4.7 g, 18.7 mmol), and sodium tert-butoxide (2.2 g, 23.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (9.1 g, 17.8 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.3 g of compound 18. (Yield 67%, MS: [M+H]) + =777).

[0308] Synthesis Example 19. Synthesis of Compound 19

[0309]

[0310] Under a nitrogen atmosphere, compound 9 (10 g, 23.7 mmol), compound amine 2 (4.2 g, 24.9 mmol), and sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (12.1 g, 23.7 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.9 g of compound 9-1. (Yield 57%, MS: [M+H)) + =511).

[0311] Under a nitrogen atmosphere, compound 9-1 (10 g, 19.6 mmol), compound J (5.2 g, 20.6 mmol), and sodium tert-butoxide (2.4 g, 25.5 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (10 g, 19.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8.5 g of compound 19. (Yield 60%, MS: [M+H)) + =727).

[0312] Synthesis Example 20. Synthesis of Compound 20

[0313]

[0314] Under a nitrogen atmosphere, compound 10 (10 g, 26.9 mmol), compound amine 17 (2.6 g, 28.2 mmol), and sodium tert-butoxide (3.4 g, 34.9 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (13.7 g, 26.9 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 6.8 g of compound 10⁻¹. (Yield 66%, MS: [M+H)) + =385).

[0315] Under a nitrogen atmosphere, compound 10⁻¹ (10 g, 26 mmol), compound K (6.9 g, 27.3 mmol), and sodium tert-butoxide (3.2 g, 33.8 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(O) (13.3 g, 26 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8.1 g of compound 20. (Yield 52%, MS: [M+H)) + =601).

[0316] Synthesis Example 21. Synthesis of Compound 21

[0317]

[0318] Under a nitrogen atmosphere, compound 11 (10 g, 22.3 mmol), compound amine 17 (2.2 g, 23.4 mmol), and sodium tert-butoxide (2.8 g, 29 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (11.4 g, 22.3 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.4 g of compound 11-1. (Yield 53%, MS: [M+H)) + =461).

[0319] Under a nitrogen atmosphere, compound 11-1 (10 g, 21.7 mmol), compound G (5.8 g, 22.8 mmol), and sodium tert-butoxide (2.7 g, 28.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (11.1 g, 21.7 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8.8 g of compound 21. (Yield 60%, MS: [M+H)) + =677).

[0320] Synthesis Example 22. Synthesis of Compound 22

[0321]

[0322] Under a nitrogen atmosphere, compound 12 (10 g, 26.9 mmol), compound amine 18 (6.9 g, 28.2 mmol), and sodium tert-butoxide (3.4 g, 34.9 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (13.7 g, 26.9 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8.3 g of compound 12-1. (Yield 58%, MS: [M+H]) + =535).

[0323] Under a nitrogen atmosphere, compound 12-1 (10 g, 18.7 mmol), compound B (5 g, 19.6 mmol), and sodium tert-butoxide (2.3 g, 24.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (9.6 g, 18.7 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 7.4 g of compound 22. (Yield 53%, MS: [M+H)) + =751).

[0324] Synthesis Example 23. Synthesis of Compound 23

[0325]

[0326] Under a nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 19 (8 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 9.4 g of compounds 1-6. (Yield 62%, MS: [M+H)) + =487).

[0327] Under a nitrogen atmosphere, compounds 1-6 (10 g, 20.5 mmol), compound L (5.8 g, 21.6 mmol), and sodium tert-butoxide (2.6 g, 26.7 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (10.5 g, 20.5 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to give 7.8 g of compound 23. (Yield 53%, MS: [M+H)) + =719).

[0328] Synthesis Example 24. Synthesis of Compound 24

[0329]

[0330] Under a nitrogen atmosphere, compounds 1-2 (10 g, 24.4 mmol), compound M (6.9 g, 25.6 mmol), and sodium tert-butoxide (3 g, 31.7 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (12.4 g, 24.4 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to give 8.9 g of compound 24. (Yield 57%, MS: [M+H)) + =643).

[0331] Synthesis Example 25. Synthesis of Compound 25

[0332]

[0333] Under a nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 20 (6 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 9 g of compounds 1-7. (Yield 68%, MS: [M+H)) + =425).

[0334] Under a nitrogen atmosphere, compounds 1-7 (10 g, 23.6 mmol), compound M (6.6 g, 24.7 mmol), and sodium tert-butoxide (2.9 g, 30.6 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (12 g, 23.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8.2 g of compound 25. (Yield 53%, MS: [M+H)) + =657).

[0335] Synthesis Example 26. Synthesis of Compound 26

[0336]

[0337] Under a nitrogen atmosphere, compound 1 (10 g, 31 mmol), compound amine 21 (9.2 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 10 g of compounds 1-8. (Yield 70%, MS: [M+H))+ =461).

[0338] Under a nitrogen atmosphere, compounds 1-8 (10 g, 21.7 mmol), compound N (6.1 g, 22.8 mmol), and sodium tert-butoxide (2.7 g, 28.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (11.1 g, 21.7 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to give 10.4 g of compound 26. (Yield 69%, MS: [M+H)) + =693).

[0339] Synthesis Example 27. Synthesis of Compound 27

[0340]

[0341] Under a nitrogen atmosphere, compound 13 (10 g, 25.1 mmol), compound amine 7 (7.1 g, 26.4 mmol), and sodium tert-butoxide (3.1 g, 32.6 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (12.8 g, 25.1 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.8 g of compound 13-1. (Yield 53%, MS: [M+H)) + =587).

[0342] Under a nitrogen atmosphere, compound 13-1 (10 g, 17 mmol), compound O (4.8 g, 17.9 mmol), and sodium tert-butoxide (2.1 g, 22.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (8.7 g, 17 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8.2 g of compound 27. (Yield 59%, MS: [M+H]) + =819).

[0343] Synthesis Example 28. Synthesis of Compound 28

[0344]

[0345] Under a nitrogen atmosphere, compound 6 (10 g, 31 mmol), compound amine 22 (8 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.8 g of compound 6-2. (Yield 58%, MS: [M+H)) + =487).

[0346] Under a nitrogen atmosphere, compound 6-2 (10 g, 20.5 mmol), compound O (5.8 g, 21.6 mmol), and sodium tert-butoxide (2.6 g, 26.7 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (10.5 g, 20.5 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8.6 g of compound 28. (Yield 58%, MS: [M+H)) + =719).

[0347] Synthesis Example 29. Synthesis of Compound 29

[0348]

[0349] Under a nitrogen atmosphere, compound 6 (10 g, 31 mmol), compound amine 23 (9.6 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 6-3. (Yield 67%, MS: [M+H)) + =537).

[0350] Under a nitrogen atmosphere, compound 6-3 (10 g, 18.6 mmol), compound P (5.3 g, 19.6 mmol), and sodium tert-butoxide (2.3 g, 24.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (9.5 g, 18.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.2 g of compound 29. (Yield 64%, MS: [M+H)) + =769).

[0351] Synthesis Example 30. Synthesis of Compound 30

[0352]

[0353] Under a nitrogen atmosphere, compound 14 (10 g, 26.9 mmol), compound amine 3 (7.6 g, 28.2 mmol), and sodium tert-butoxide (3.4 g, 34.9 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (13.7 g, 26.9 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.5 g of compound 14-1. (Yield 63%, MS: [M+H]) + =561).

[0354] Under a nitrogen atmosphere, compound 14-1 (10 g, 17.8 mmol), compound Q (5 g, 18.7 mmol), and sodium tert-butoxide (2.2 g, 23.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (9.1 g, 17.8 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.7 g of compound 30. (Yield 69%, MS: [M+H)) + =793).

[0355] Synthesis Example 31. Synthesis of Compound 31

[0356]

[0357] Under a nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 24 (10.5 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to give 7.1 g of compounds 4-6. (Yield 52%, MS: [M+H)) + =441).

[0358] Under a nitrogen atmosphere, compounds 4-6 (10 g, 22.7 mmol), compound R (6.4 g, 23.8 mmol), and sodium tert-butoxide (2.8 g, 29.5 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (11.6 g, 22.7 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.9 g of compound 31. (Yield 65%, MS: [M+H)) + =673).

[0359] Synthesis Example 32. Synthesis of Compound 32

[0360]

[0361] Under a nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 25 (4.7 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 6 g of compounds 4-7. (Yield 50%, MS: [M+H)) + =385).

[0362] Under a nitrogen atmosphere, compounds 4-7 (10 g, 26 mmol), compound M (7.3 g, 27.3 mmol), and sodium tert-butoxide (3.2 g, 33.8 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (13.3 g, 26 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8.8 g of compound 32. (Yield 55%, MS: [M+H)) + =617).

[0363] Synthesis Example 33. Synthesis of Compound 33

[0364]

[0365] Under a nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 26 (8.8 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 10.5 g of compounds 4-8. (Yield 66%, MS: [M+H)) + =511).

[0366] Under a nitrogen atmosphere, compounds 4-8 (10 g, 19.6 mmol), compound N (5.5 g, 20.6 mmol), and sodium tert-butoxide (2.4 g, 25.5 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (10 g, 19.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 7.6 g of compound 33. (Yield 52%, MS: [M+H]) + =743).

[0367] Synthesis Example 34. Synthesis of Compound 34

[0368]

[0369] Under a nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 20 (6 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compounds were purified by silica gel column chromatography to obtain 8.4 g of compounds 4-9. (Yield 64%, MS: [M+H)) + =425).

[0370] Under a nitrogen atmosphere, compounds 4-9 (10 g, 23.6 mmol), compound S (6.6 g, 24.7 mmol), and sodium tert-butoxide (2.9 g, 30.6 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (12 g, 23.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compounds were then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 7.9 g of compound 34. (Yield 51%, MS: [M+H)) + =657).

[0371] Synthesis Example 35. Synthesis of Compound 35

[0372]

[0373] Under a nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 27 (8 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.4 g of compound 4-10. (Yield 69%, MS: [M+H)) + =487).

[0374] Under a nitrogen atmosphere, compound 4-10 (10 g, 20.5 mmol), compound P (5.8 g, 21.6 mmol), and sodium tert-butoxide (2.6 g, 26.7 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (10.5 g, 20.5 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.7 g of compound 35. (Yield 66%, MS: [M+H]) + =719).

[0375] Synthesis Example 36. Synthesis of Compound 36

[0376]

[0377] Under a nitrogen atmosphere, compounds 4-9 (10 g, 22.7 mmol), compound T (6.4 g, 23.8 mmol), and sodium tert-butoxide (2.8 g, 29.5 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (11.6 g, 22.7 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8.8 g of compound 36. (Yield 58%, MS: [M+H)) + =673).

[0378] Synthesis Example 37. Synthesis of Compound 37

[0379]

[0380] Under a nitrogen atmosphere, compound 4 (10 g, 31 mmol), compound amine 28 (9.6 g, 32.6 mmol), and sodium tert-butoxide (3.9 g, 40.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (15.9 g, 31 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.5 g of compound 4-11. (Yield 63%, MS: [M+H)) + =537).

[0381] Under a nitrogen atmosphere, compound 4-11 (10 g, 18.6 mmol), compound U (5.3 g, 19.6 mmol), and sodium tert-butoxide (2.3 g, 24.2 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (9.5 g, 18.6 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 7.4 g of compound 37. (Yield 52%, MS: [M+H]) + =769).

[0382] Synthesis Example 38. Synthesis of Compound 38

[0383]

[0384] Under a nitrogen atmosphere, compound 15 (10 g, 23.7 mmol), compound amine 29 (6.7 g, 24.9 mmol), and sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (12.1 g, 23.7 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 9.7 g of compound 15-1. (Yield 67%, MS: [M+H))+ =611).

[0385] Under a nitrogen atmosphere, compound 15-1 (10 g, 16.4 mmol), compound V (4.6 g, 17.2 mmol), and sodium tert-butoxide (2 g, 21.3 mmol) were added to 200 mL of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(O) (8.4 g, 16.4 mmol) was added. After 5 hours, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform, washed twice with water, and the organic layer was separated. After treatment with anhydrous magnesium sulfate, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 8 g of compound 38. (Yield 58%, MS: [M+H)) + =843).

[0386] Example 1

[0387] A glass substrate coated with an ITO (indium tin oxide) film at a thickness of 1000 Å was immersed in distilled water containing detergent and ultrasonically washed. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the ultrasonic washing was repeated twice with distilled water for 10 minutes each time. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0388] On the prepared ITO transparent electrode, as a hole injection layer, compound HI-1 is thermally vacuum-deposited to a thickness of 1150 Å to form a hole injection layer, and compound A-1 is p-doped at a concentration of 1.5%. On the hole injection layer, compound HT-1 is vacuum-deposited to form a hole transport layer with a thickness of 800 Å. Next, on the hole transport layer, compound 1 is vacuum-deposited to a thickness of 150 Å to form an electron suppression layer. Then, on the vapor-deposited film of compound 1, compound RH-1 (as the main component) and compound Dp-7 (as the dopant) are vacuum-deposited at a weight ratio of 98:2 to form a red emitting layer with a thickness of 400 Å. On the emitting layer, compound HB-1 is vacuum-deposited to a thickness of 30 Å to form a hole blocking layer. Next, on the hole-blocking layer, the following compounds ET-1 and LiQ are vacuum-deposited in a 2:1 weight ratio to form an electron injection and transport layer with a thickness of 300 Å. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially deposited with a thickness of 12 Å and aluminum with a thickness of 1000 Å to form a cathode.

[0389]

[0390] During the above process, the evaporation rate of organic materials was maintained at 0.4 Å / s to 0.7 Å / s, the evaporation rate of lithium fluoride at the cathode was maintained at 0.3 Å / s, and the evaporation rate of aluminum was maintained at 2 Å / s. During evaporation, the vacuum level was maintained at 2 x 10⁻⁶. -7 Up to 5x10 -6 This led to the creation of organic light-emitting devices.

[0391] Examples 2 to 38

[0392] In the organic light-emitting device of Example 1, compounds 2 to 22 as described in Table 1 below were used instead of compound 1, and the organic light-emitting device was otherwise manufactured by the same method as in Example 1 above.

[0393]

[0394]

[0395] .

[0396] Comparative Examples 1 to 10

[0397] In the organic light-emitting device of Example 1, the compounds listed in Table 1 below were used instead of compound 1. Otherwise, the organic light-emitting device was manufactured by the same method as in Example 1 above. The compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, and C-10 used in Table 1 below are shown below.

[0398] .

[0399] When an electric current was applied to the organic light-emitting devices manufactured in Examples 1 to 38 and Comparative Examples 1 to 10, the voltage and efficiency (10 mA / cm²) were measured. 2 The results are shown in Table 1 below. Lifetime T95 refers to the time (hr) required for the brightness to decrease from the initial brightness (5000 nits) to 95%.

[0400] [Table 1]

[0401]

[0402]

[0403] When current was applied to the organic light-emitting devices fabricated in Examples 1 to 38 and Comparative Examples 1 to 10, the results shown in Table 1 were obtained. The red organic light-emitting device of Example 1 used a material widely used in the past, and was a dopant structure in which compound 1 was used as an electron suppression layer and Dp-7 was used as a red light-emitting layer. Comparative Examples 1 to 10 used C-1 to C-10 instead of compound 1 to fabricate organic light-emitting devices.

[0404] As shown in Table 1 above, it can be seen that, according to the present invention, the organic light-emitting devices of Examples 1 to 38, which use compounds represented by Chemical Formula 1 (i.e., compounds with a polycyclic structure in which a tertiary amine group of benzo[a]naphthofuran] or benzo[a]naphthothiophene] is attached at a specific position of the parent structure of a carbazole-based polycyclic ring with a specific structure, as the electron suppression layer, exhibit significantly lower driving voltage and improved efficiency compared to the organic light-emitting devices of Comparative Examples 1 to 10 manufactured using the compounds of C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, and C-10 described above. This demonstrates that energy transfer from the host to the red dopant is well formed. Furthermore, it can be seen that the organic light-emitting devices of Examples 1 to 38 can significantly improve lifetime characteristics while maintaining high efficiency. This can ultimately be attributed to the fact that, compared to the compounds of the comparative examples, the compounds of the embodiments according to the present invention have higher stability for electrons and holes. In summary, it can be confirmed that using the compounds of the present invention as an electron suppression layer of the red emitting layer can improve the driving voltage, luminous efficiency, and lifetime characteristics of organic light-emitting devices.

[0405] [Symbol Explanation]

[0406] 1: Substrate 2: Anode

[0407] 3: Light-emitting layer 4: Cathode

[0408] 5: Hole injection layer; 6: Hole transport layer

[0409] 7: Electron suppression layer; 8: Hole blocking layer

[0410] 9: Electron injection and transport layer.

Claims

1. A compound represented by the following chemical formula 1: Chemical Formula 1 In the chemical formula 1, A and B are each independently benzene rings fused with adjacent rings. Both n1 and n2 are 0, or one of n1 and n2 is 1 and the others are 0. Ar1 is phenyl, biphenyl, or naphthyl. L1 is a single bond or a phenylene oxide. R1 can be either hydrogen or deuterium independently. R2 atoms can be hydrogen or deuterium independently; or they can combine with each other to form a benzene ring. One of R3 is a substituent represented by the following chemical formula 2, and the rest are hydrogen or deuterium. Chemical formula 2 In the chemical formula 2, L2 can be a single bond, phenylene, biphenylene, terphenylene, tetraphenylene, or naphthylene. Ar2 is a triphenyl, tetraphenyl, naphthyl-substituted phenyl, naphthyl-substituted biphenyl, phenyl-substituted naphthyl, naphthyl-substituted naphthyl, phenyl-substituted phenanthrene, or triphenylene, and Ar2 is either deuterium-substituted or unsubstituted. Ar3 is a substituent represented by any one of the following chemical formulas 3-1 to 3-6. In the chemical formulas 3-1 to 3-6, X is O or S, and Ar3 may or may not be replaced by deuterium. But Ar3 is not .

2. The compound according to claim 1, wherein, The compound represented by chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-20 and 1-33 to 1-41: In the chemical formulas 1-1 to 1-20 and 1-33 to 1-41, Ar1, L1, and R3 are the same as defined in claim 1.

3. The compound according to claim 1, wherein, Ar2 is selected from any one of the following groups: 。 4. The compound according to claim 1, wherein, Ar3 is selected from any one of the following groups: 。 5. A compound selected from any one of the following compounds: 。 6. An organic light-emitting device, wherein, include: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 5.

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

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