ORGANIC LIGHT EMITTING DEVICE

Abstract

An organic light emitting device having improved driving voltage, efficiency and lifetime. The device includes a light emitting layer containing a compound of Chemical Formulae 1 and 2:

##STR00001## wherein: X.sub.1-X.sub.7 are each independently CR.sub.1 or N, at least one of X.sub.1-X.sub.7 is N, and each R.sub.1 is independently hydrogen, deuterium, or a substituted or unsubstituted C.sub.6-60 aryl or C.sub.2-60 heteroaryl containing any one or more of N, O and S; Ar.sub.1 and Ar.sub.2 are each independently a substituted or unsubstituted C.sub.6-60 aryl or C.sub.2-60 heteroaryl containing at least one of N, O and S; A and B are each independently hydrogen, deuterium,

##STR00002## or a substituted or unsubstituted C.sub.6-60 aryl or C.sub.2-60 heteroaryl containing at least one of N, O and S, provided that at least one of A and B is

##STR00003## and the other substituents are described in the specification.

Claims

1. An organic light emitting device comprising: an anode; a cathode; and a light emitting layer interposed between the anode and the cathode, wherein the light emitting layer includes a compound of the following Chemical Formula 1 and a compound of the following Chemical Formula 2: ##STR00544## wherein in Chemical Formula 1: X.sub.1 to X.sub.7 are each independently CR.sub.1 or N, provided that at least one of X.sub.1 to X.sub.7 is N; each R.sub.1 is independently hydrogen, deuterium, a substituted or unsubstituted C.sub.6-60 aryl, or a substituted or unsubstituted C.sub.2-60 heteroaryl containing any one or more selected from the group consisting of N, O and S; L.sub.1 to L.sub.3 are each independently a single bond, a substituted or unsubstituted C.sub.6-60 arylene, or a substituted or unsubstituted C.sub.2-60 heteroarylene containing at least one selected from the group consisting of N, O and S; and Ar.sub.1 and Ar.sub.2 are each independently a substituted or unsubstituted C.sub.6-60 aryl or a substituted or unsubstituted C.sub.2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S; ##STR00545## wherein in Chemical Formula 2: L.sub.4 and L.sub.5 are each independently a single bond, a substituted or unsubstituted C.sub.6-60 arylene, or a substituted or unsubstituted C.sub.2-60 heteroarylene containing at least one heteroatom selected from the group consisting of N, O and S; A and B are each independently hydrogen, deuterium, ##STR00546## a substituted or unsubstituted C.sub.6-60 aryl, or a substituted or unsubstituted C.sub.2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S, provided that at least one of A and B is ##STR00547## L.sub.6 and L.sub.7 are each independently a single bond, a substituted or unsubstituted C.sub.6-60 arylene, or a substituted or unsubstituted C.sub.2-60 heteroarylene containing at least one heteroatom selected from the group consisting of N, O and S; Ar.sub.3 and Ar.sub.4 are each independently a substituted or unsubstituted C.sub.6-60 aryl or a substituted or unsubstituted C.sub.2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S; each R.sub.2 is independently hydrogen or deuterium; and a is an integer of 0 to 8.

2. The organic light emitting device according to claim 1, wherein: any one of X.sub.1 to X.sub.7 is N, and the rest are CR.sub.1.

3. The organic light emitting device according to claim 1, wherein: R.sub.1 is hydrogen, deuterium, phenyl, biphenylyl, naphthyl, carbazolyl, fluoranthenyl, phenanthrenyl, triphenylenyl, benzo[a]carbazolyl, benzo[b]carbazolyl, benzo[c]carbazolyl, dibenzofuranyl, benzo[d]naphtho[1,2-b]furanyl, benzo[d]naphtho[2,3-b]furanyl, benzo[d]naphtho[2,1-b]furanyl, benzo[d]naphtho[1,2-b]thiophenyl, benzo[d]naphtho[2,3-b]thiophenyl, benzo[d]naphtho[2,1-b]thiophenyl, benzo[c]phenanthrenyl, chrysenyl, phenyl naphthyl, or naphthyl phenyl, provided that when the R.sub.1 is not hydrogen or deuterium, R.sub.1 is unsubstituted or substituted with at least one deuterium.

4. The organic light emitting device according to claim 1, wherein: L.sub.1 to L.sub.3 are each independently a single bond, phenylene, naphthalendiyl, ##STR00548## provided that when the L.sub.1 to L.sub.3 are not a single bond, L.sub.1 to L.sub.3 are unsubstituted or substituted with at least one deuterium.

5. The organic light emitting device according to claim 1, wherein: Ar.sub.1 and Ar.sub.2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, fluoranthenyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, chrysenyl, or benzo[c]phenanthrenyl, and the Ar.sub.1 and Ar.sub.2 are unsubstituted or substituted with at least one deuterium.

6. The organic light emitting device according to claim 1, wherein: the compound of Chemical Formula 1 is any one compound selected from the group consisting of: ##STR00549## ##STR00550## ##STR00551## ##STR00552## ##STR00553## ##STR00554## ##STR00555## ##STR00556## ##STR00557## ##STR00558## ##STR00559## ##STR00560## ##STR00561## ##STR00562## ##STR00563## ##STR00564## ##STR00565## ##STR00566## ##STR00567## ##STR00568## ##STR00569## ##STR00570## ##STR00571## ##STR00572## ##STR00573## ##STR00574## ##STR00575## ##STR00576## ##STR00577## ##STR00578## ##STR00579## ##STR00580## ##STR00581## ##STR00582## ##STR00583## ##STR00584## ##STR00585## ##STR00586## ##STR00587## ##STR00588## ##STR00589## ##STR00590## ##STR00591## ##STR00592## ##STR00593## ##STR00594## ##STR00595## ##STR00596## ##STR00597## ##STR00598## ##STR00599## ##STR00600## ##STR00601## ##STR00602## ##STR00603## ##STR00604## ##STR00605## ##STR00606## ##STR00607## ##STR00608## ##STR00609## ##STR00610## ##STR00611## ##STR00612## ##STR00613## ##STR00614## ##STR00615## ##STR00616## ##STR00617## ##STR00618## ##STR00619## ##STR00620## ##STR00621## ##STR00622## ##STR00623## ##STR00624## ##STR00625## ##STR00626## ##STR00627## ##STR00628## ##STR00629## ##STR00630## ##STR00631## ##STR00632## ##STR00633## ##STR00634## ##STR00635## ##STR00636## ##STR00637## ##STR00638## ##STR00639## ##STR00640## ##STR00641## ##STR00642## ##STR00643## ##STR00644## ##STR00645## ##STR00646## ##STR00647## ##STR00648## ##STR00649## ##STR00650## ##STR00651## ##STR00652## ##STR00653## ##STR00654## ##STR00655## ##STR00656## ##STR00657## ##STR00658## ##STR00659## ##STR00660## ##STR00661## ##STR00662## ##STR00663## ##STR00664## ##STR00665## ##STR00666## ##STR00667## ##STR00668## ##STR00669## ##STR00670## ##STR00671## ##STR00672## ##STR00673## ##STR00674## ##STR00675## ##STR00676## ##STR00677## ##STR00678## ##STR00679## ##STR00680## ##STR00681## ##STR00682## ##STR00683## ##STR00684## ##STR00685## ##STR00686## ##STR00687## ##STR00688## ##STR00689## ##STR00690## ##STR00691## ##STR00692## ##STR00693## ##STR00694## ##STR00695## ##STR00696## ##STR00697## ##STR00698## ##STR00699## ##STR00700## ##STR00701## ##STR00702## ##STR00703## ##STR00704## ##STR00705## ##STR00706## ##STR00707## ##STR00708## ##STR00709## ##STR00710## ##STR00711## ##STR00712## ##STR00713## ##STR00714## ##STR00715## ##STR00716## ##STR00717## ##STR00718## ##STR00719## ##STR00720## ##STR00721## ##STR00722## ##STR00723## ##STR00724## ##STR00725## ##STR00726## ##STR00727## ##STR00728## ##STR00729## ##STR00730## ##STR00731## ##STR00732## ##STR00733## ##STR00734## ##STR00735## ##STR00736## ##STR00737## ##STR00738## ##STR00739## ##STR00740## ##STR00741## ##STR00742## ##STR00743## ##STR00744## ##STR00745## ##STR00746## ##STR00747## ##STR00748## ##STR00749## ##STR00750## ##STR00751## ##STR00752## ##STR00753## ##STR00754## ##STR00755## ##STR00756## ##STR00757## ##STR00758## ##STR00759## ##STR00760## ##STR00761## ##STR00762## ##STR00763## ##STR00764## ##STR00765## ##STR00766## ##STR00767## ##STR00768## ##STR00769## ##STR00770## ##STR00771## ##STR00772## ##STR00773## ##STR00774## ##STR00775## ##STR00776## ##STR00777## ##STR00778## ##STR00779## ##STR00780## ##STR00781## ##STR00782## ##STR00783## ##STR00784## ##STR00785## ##STR00786## ##STR00787## ##STR00788## ##STR00789## ##STR00790## ##STR00791## ##STR00792## ##STR00793## ##STR00794## ##STR00795## ##STR00796## ##STR00797## ##STR00798## ##STR00799## ##STR00800## ##STR00801## ##STR00802## ##STR00803## ##STR00804## ##STR00805## ##STR00806## ##STR00807## ##STR00808## ##STR00809## ##STR00810## ##STR00811## ##STR00812## ##STR00813## ##STR00814## ##STR00815## ##STR00816## ##STR00817## ##STR00818## ##STR00819## ##STR00820## ##STR00821## ##STR00822## ##STR00823## ##STR00824## ##STR00825## ##STR00826## ##STR00827## ##STR00828##

7. The organic light emitting device according to claim 1, wherein: L.sub.4 and L.sub.5 are each independently a single bond, phenylene, biphenyldiyl, or phenylene substituted with 4 deuteriums.

8. The organic light emitting device according to claim 1, wherein: A and B are each independently hydrogen, phenyl that is unsubstituted or substituted with 1 to 5 deuteriums or ##STR00829## provided that at least one of A and B is ##STR00830##

9. The organic light emitting device according to claim 1, wherein: A is ##STR00831## and B is hydrogen or phenyl that is unsubstituted or substituted with 1 to 5 deuteriums.

10. The organic light emitting device according to claim 1, wherein: L.sub.6 and L.sub.7 are each independently a single bond, phenylene, biphenyldiyl, or phenylene substituted with 4 deuteriums.

11. The organic light emitting device according to claim 1, wherein: Ar.sub.3 and Ar.sub.4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenyl naphthyl, phenanthrenyl, triphenylenyl, phenyl phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, methyl dibenzofluorenyl, carbazolyl, phenyl carbazolyl, phenyl substituted with 5 deuteriums, biphenylyl substituted with 4 deuteriums, biphenylyl substituted with 9 deuteriums, or terphenylyl substituted with 4 deuteriums.

12. The organic light emitting device according to claim 1, wherein: the compound of Chemical Formula 2 is any one compound selected from the group consisting of: ##STR00832## ##STR00833## ##STR00834## ##STR00835## ##STR00836## ##STR00837## ##STR00838## ##STR00839## ##STR00840## ##STR00841## ##STR00842## ##STR00843## ##STR00844## ##STR00845## ##STR00846## ##STR00847## ##STR00848## ##STR00849## ##STR00850## ##STR00851## ##STR00852## ##STR00853## ##STR00854## ##STR00855## ##STR00856## ##STR00857## ##STR00858## ##STR00859## ##STR00860## ##STR00861## ##STR00862## ##STR00863## ##STR00864## ##STR00865## ##STR00866## ##STR00867## ##STR00868## ##STR00869## ##STR00870## ##STR00871## ##STR00872## ##STR00873## ##STR00874## ##STR00875## ##STR00876## ##STR00877## ##STR00878## ##STR00879## ##STR00880## ##STR00881## ##STR00882## ##STR00883## ##STR00884## ##STR00885## ##STR00886## ##STR00887## ##STR00888## ##STR00889## ##STR00890## ##STR00891## ##STR00892## ##STR00893## ##STR00894## ##STR00895## ##STR00896## ##STR00897## ##STR00898## ##STR00899## ##STR00900## ##STR00901## ##STR00902## ##STR00903## ##STR00904## ##STR00905## ##STR00906## ##STR00907## ##STR00908## ##STR00909## ##STR00910## ##STR00911## ##STR00912## ##STR00913## ##STR00914## ##STR00915## ##STR00916## ##STR00917## ##STR00918## ##STR00919## ##STR00920## ##STR00921## ##STR00922## ##STR00923## ##STR00924## ##STR00925## ##STR00926## ##STR00927## ##STR00928## ##STR00929## ##STR00930## ##STR00931## ##STR00932## ##STR00933## ##STR00934## ##STR00935## ##STR00936## ##STR00937## ##STR00938## ##STR00939## ##STR00940## ##STR00941## ##STR00942## ##STR00943## ##STR00944## ##STR00945## ##STR00946## ##STR00947## ##STR00948## ##STR00949## ##STR00950## ##STR00951## ##STR00952## ##STR00953## ##STR00954## ##STR00955## ##STR00956## ##STR00957## ##STR00958## ##STR00959## ##STR00960## ##STR00961## ##STR00962## ##STR00963## ##STR00964## ##STR00965## ##STR00966## ##STR00967## ##STR00968## ##STR00969## ##STR00970## ##STR00971## ##STR00972## ##STR00973## ##STR00974## ##STR00975## ##STR00976## ##STR00977## ##STR00978## ##STR00979## ##STR00980## ##STR00981## ##STR00982## ##STR00983## ##STR00984## ##STR00985## ##STR00986## ##STR00987## ##STR00988## ##STR00989## ##STR00990## ##STR00991## ##STR00992## ##STR00993## ##STR00994## ##STR00995## ##STR00996## ##STR00997## ##STR00998## ##STR00999## ##STR01000## ##STR01001## ##STR01002## ##STR01003## ##STR01004## ##STR01005## ##STR01006## ##STR01007## ##STR01008## ##STR01009## ##STR01010## ##STR01011## ##STR01012## ##STR01013## ##STR01014## ##STR01015## ##STR01016## ##STR01017## ##STR01018## ##STR01019## ##STR01020## ##STR01021## ##STR01022## ##STR01023## ##STR01024## ##STR01025## ##STR01026## ##STR01027##

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0027] FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.

[0028] FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4.

DETAILED DESCRIPTION

[0029] Hereinafter, embodiments of the present disclosure will be described in more detail to facilitate understanding of the invention.

[0030] As used herein, the notation or means a bond linked to another substituent group.

[0031] As used herein, the term substituted or unsubstituted means being unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxy group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthioxy group, an arylthioxy group, an alkylsulfoxy group, an arylsulfoxy group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heteroaryl containing at least one of N, O and S atoms, or being unsubstituted or substituted with a substituent to which two or more substituents of the above-exemplified substituents are connected. For example, a substituent in which two or more substituents are connected can be a biphenyl group. Namely, a biphenyl group can be an aryl group, or it can be interpreted as a substituent in which two phenyl groups are connected.

[0032] In the present disclosure, the carbon number of a carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group can be a substituent having the following structural formulas, but is not limited thereto:

##STR00008##

[0033] In the present disclosure, an ester group can have a structure in which oxygen of the ester group can be substituted by a straight-chain, branched-chain, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group can be a substituent having the following structural formulas, but is not limited thereto:

##STR00009##

[0034] In the present disclosure, the carbon number of an imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group can be a substituent having the following structural formulas, but is not limited thereto:

##STR00010##

[0035] In the present disclosure, a silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like, but is not limited thereto.

[0036] In the present disclosure, a boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group, but is not limited thereto.

[0037] In the present disclosure, examples of a halogen group include fluorine, chlorine, bromine, or iodine.

[0038] In the present disclosure, the alkyl group can be straight-chain or branched-chain, and the carbon number thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

[0039] In the present disclosure, the alkenyl group can be straight-chain or branched-chain, and the carbon number thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to still another embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples thereof 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, a stilbenyl group, a styrenyl group, and the like, but are not limited thereto.

[0040] In the present disclosure, a cycloalkyl group is not particularly limited, but the carbon number thereof is preferably 3 to 60. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to still another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

[0041] In the present disclosure, an aryl group is not particularly limited, but the carbon number thereof is preferably 6 to 60, and it can be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group can be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. The polycyclic aryl group includes a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, or the like, but is not limited thereto.

[0042] In the present disclosure, the fluorenyl group can be substituted, and two substituents can be linked with each other to form a spiro structure. In the case where the fluorenyl group is substituted,

##STR00011##

and the like can be formed. However, the structure is not limited thereto.

[0043] In the present disclosure, a heteroaryl group is a heteroaryl group containing one or more of O, N, Si and S as a heteroatom, and the carbon number thereof is not particularly limited, but is preferably 2 to 60. According to one embodiment, the carbon number of the heteroaryl group is 6 to 30. According to one embodiment, the carbon number of the heteroaryl group is 6 to 20. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazol group, an oxadiazol group, a triazol group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazol group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a dibenzofuranyl group, and the like, but are not limited thereto.

[0044] In the present disclosure, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned examples of the aryl group. In the present disclosure, the alkyl group in the aralkyl group, the alkylaryl group and the alkylamine group is the same as the aforementioned examples of the alkyl group. In the present disclosure, the heteroaryl in the heteroarylamine can be applied to the aforementioned description of the heteroaryl group. In the present disclosure, the alkenyl group in the aralkenyl group is the same as the aforementioned examples of the alkenyl group. In the present disclosure, the aforementioned description of the aryl group can be applied except that the arylene is a divalent group. In the present disclosure, the aforementioned description of the heteroaryl group can be applied except that the heteroarylene is a divalent group. In the present disclosure, the aforementioned description of the aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group but formed by combining two substituent groups. In the present disclosure, the aforementioned description of the heteroaryl group can be applied, except that the heteroaryl is not a monovalent group but formed by combining two substituent groups.

[0045] Hereinafter, the present disclosure will be described in detail for each configuration.

Anode and Cathode

[0046] An anode and a cathode used in the present disclosure mean electrodes used in an organic light emitting device.

[0047] As the anode material, generally, a material having a large work function is preferably used so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chrome, copper, zinc, and gold, or an alloy thereof; metal oxides such as zinc oxides, indium oxides, indium tin oxides (ITO), and indium zinc oxides (IZO); a combination of metals and oxides, such as ZnO:Al or SNO.sub.2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, and the like, but are not limited thereto.

[0048] As the cathode material, generally, a material having a small work function is preferably used so that electrons can be easily injected into the organic material 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 an alloy thereof; a multilayered structure material such as LiF/Al or LiO.sub.2/Al, and the like, but are not limited thereto.

Hole Injection Layer

[0049] The organic light emitting device according to the present disclosure can further include a hole injection layer on the anode, if necessary.

[0050] The hole injection layer is a layer injecting holes from an electrode, and the hole injection material is preferably a compound which has a capability of transporting the holes, has a hole injection effect in the anode and an excellent hole injection effect to the light emitting layer or the light emitting material, prevents movement of an exciton generated in the light emitting layer to the electron injection layer or the electron injection material, and is excellent in the ability to form a thin film. Further, it is preferable that a HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and a HOMO of a peripheral organic material layer.

[0051] Specific examples of the hole injection material include metal porphyrine, oligothiophene, an arylamine-based organic material, a hexanitrilehexaazatriphenylene-based organic material, a quinacridone-based organic material, a perylene-based organic material, anthraquinone, polyaniline and polythiophene-based conductive polymer, and the like, but are not limited thereto.

Hole Transport Layer

[0052] The organic light emitting device according to the present disclosure can include a hole transport layer on the anode (or on the hole injection layer if the hole injection layer exists), if necessary.

[0053] The hole transport layer is a layer that receives holes from a hole injection layer and transports the holes to the light emitting layer. The hole transport material is suitably a material having large mobility to the holes, which can receive injection of holes from the anode or the hole injection layer and transfer the holes to the light emitting layer.

[0054] Specific examples of the hole transport material include an arylamine-based organic material, a conductive polymer, a block copolymer in which a conjugate portion and a non-conjugate portion are present together, and the like, but are not limited thereto.

Electron Blocking Layer

[0055] The organic light emitting device according to the present disclosure includes an electron blocking layer on the hole transport layer, if necessary.

[0056] The electron blocking layer means a layer provided between the hole transport layer and the light emitting layer in order to prevent the electrons injected in the cathode from being transferred to the hole transport layer without being recombined in the light emitting layer, which can also be referred to as an electron stopping layer or an electron inhibition layer. The electron blocking layer is preferably a material having the smaller electron affinity than the electron transport layer.

Light Emitting Layer

[0057] The light emitting layer used in the present disclosure is a layer that can emit light in the visible light region by combining holes and electrons transported from the anode and the cathode. Generally, the light emitting layer includes a host material and a dopant material, and in the present disclosure, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are included as a host

[0058] Preferably, any one of X.sub.1 to X.sub.7 is N, and the rest can be CR.sub.1.

[0059] Preferably, the Chemical Formula 1 can be any one of the following Chemical Formula 1-1 to Chemical Formula 1-7:

##STR00012## ##STR00013## [0060] wherein in Chemical Formula-1 to Chemical Formula 1-7, [0061] R.sub.1, L.sub.1 to L.sub.3, Ar.sub.1 and Ar.sub.2 are as defined in Chemical Formula 1.

[0062] Preferably, each R.sub.1 can be independently hydrogen, deuterium, a substituted or unsubstituted C.sub.6-20 aryl, or a substituted or unsubstituted C.sub.2-20 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S. More preferably, R.sub.1 is hydrogen, deuterium, phenyl, biphenylyl, naphthyl, carbazolyl, fluoranthenyl, phenanthrenyl, triphenylenyl, benzo[a]carbazolyl, benzo[b]carbazolyl, benzo[c]carbazolyl, dibenzofuranyl, benzo[d]naphtho[1,2-b]furanyl, benzo[d]naphtho[2,3-b]furanyl, benzo[d]naphtho[2,1-b]furanyl, benzo[d]naphtho[1,2-b]thiophenyl, benzo[d]naphtho[2,3-b]thiophenyl, benzo[d]naphtho[2,1-b]thiophenyl, benzo[c]phenanthrenyl, chrysenyl, phenyl naphthyl, or naphthyl phenyl, provided that when the R.sub.1 is not hydrogen or deuterium, R.sub.1 is unsubstituted or substituted with at least one deuterium.

[0063] Preferably, one of R.sub.1 is phenyl, biphenylyl, naphthyl, carbazolyl, fluoranthenyl, phenanthrenyl, triphenylenyl, benzo[a]carbazolyl, benzo[b]carbazolyl, benzo[c]carbazolyl, dibenzofuranyl, benzo[d]naphtho[1,2-b]furanyl, benzo[d]naphtho[2,3-b]furanyl, benzo[d]naphtho[2,1-b]furanyl, benzo[d]naphtho[1,2-b]thiophenyl, benzo[d]naphtho[2,3-b]thiophenyl, benzo[d]naphtho[2,1-b]thiophenyl, benzo[c]phenanthrenyl, chrysenyl, phenyl naphthyl, or naphthyl phenyl, and the other R.sub.1s can be hydrogen or deuterium, or each R.sub.1 can be independently hydrogen or deuterium.

[0064] Preferably, L.sub.1 to L.sub.3 are each independently a single bond, a substituted or unsubstituted C.sub.6-20 arylene, or a substituted or unsubstituted C.sub.2-20 heteroarylene containing at least one heteroatom selected from the group consisting of N, O and S. More preferably, L.sub.1 to L.sub.3 are each independently a single bond, phenylene, naphthalenediyl,

##STR00014## [0065] provided that when the L.sub.1 to L.sub.3 are not a single bond, L.sub.1 to L.sub.3 are unsubstituted or substituted with at least one deuterium.

[0066] Preferably, L.sub.1 is a single bond, naphthalendiyl,

##STR00015##

and L.sub.2 and L.sub.3 can be each independently a single bond, phenylene, naphthalendiyl,

##STR00016##

[0067] Preferably, Ar.sub.1 and Ar.sub.2 can be each independently a substituted or unsubstituted C.sub.6-20 aryl or a substituted or unsubstituted C.sub.2-20 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S. More preferably, Ar.sub.1 and Ar.sub.2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, fluoranthenyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, chrysenyl, or benzo[c]phenanthrenyl, provided that the Ar.sub.1 and Ar.sub.2 can be unsubstituted or substituted with at least one deuterium.

[0068] Representative examples of the compound of Chemical Formula 1 are as follows:

##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052##

##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118##

##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154##

##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188##

##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251## ##STR00252## ##STR00253## ##STR00254## ##STR00255## ##STR00256##

[0069] The compound of Chemical Formula 1 wherein X.sub.1 is N, X.sub.2 is CR.sub.1, and X.sub.3 to X.sub.7 are CH can be prepared by a preparation method as shown in the following Reaction Scheme 1-1 as an example, the compound wherein X.sub.1 is N, and X.sub.2 to X.sub.7 is CH can be prepared by a preparation method as shown in the following Reaction Scheme 1-2 as an example, and the other remaining compounds can be prepared in a similar manner.

##STR00257##

##STR00258##

[0070] In Reaction Schemes 1-1 and 1-2, R.sub.1, L.sub.1 to L.sub.3, Ar.sub.1 and Ar.sub.2 are the same as defined in Chemical Formula 1, Z.sub.1 and Z.sub.2 are each independently halogen, preferably Z.sub.1 and Z.sub.2 are each independently chloro or bromo.

[0071] Reaction Schemes 1-1 and 1-2 are Suzuki coupling reactions, which are preferably carried out in the presence of a palladium catalyst and a base, and a reactive group for the Suzuki coupling reaction can be modified as known in the art. In addition, if necessary, an amine substitution reaction can be accompanied, and in this case, it is preferably carried out in the presence of a palladium catalyst and a base, and a reactive group for the amine substitution reaction can be modified as known in the art. The preparation method can be further embodied in the Preparation Examples described hereinafter.

[0072] Preferably, L.sub.4 and L.sub.5 are each independently a single bond, a substituted or unsubstituted C.sub.6-20 arylene, or a substituted or unsubstituted C.sub.2-20 heteroarylene containing at least one heteroatom selected from the group consisting of N, O and S. Preferably, L.sub.4 and L.sub.5 can be each independently a single bond, phenylene that is unsubstituted or substituted with 1 to 4 deuteriums, or biphenyldiyl that is unsubstituted or substituted with 1 to 8 deuteriums. More preferably, L.sub.4 and L.sub.5 can be each independently a single bond, phenylene, biphenyldiyl, or phenylene substituted with 4 deuteriums.

[0073] Preferably, A and B are each independently hydrogen, deuterium,

##STR00259##

a substituted or unsubstituted C.sub.6-20 aryl, or a substituted or unsubstituted C.sub.2-20 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S, provided that at least one of A and B are

##STR00260##

More preferably, A and B are each independently hydrogen, phenyl that is unsubstituted or substituted with 1 to 5 deuteriums, or

##STR00261##

provided that at least one of A and B is

##STR00262##

More preferably, A is

##STR00263##

B can be hydrogen or phenyl that is unsubstituted or substituted with 1 to 5 deuteriums. Most preferably, A is

##STR00264##

and B can be hydrogen or phenyl.

[0074] Preferably, L.sub.6 and L.sub.7 can be each independently a single bond, a substituted or unsubstituted C.sub.6-20 arylene, or a substituted or unsubstituted C.sub.2-20 heteroarylene containing at least one heteroatom selected from the group consisting of N, O and S. Preferably, L.sub.6 and L.sub.7 can be each independently a single bond, phenylene that is unsubstituted or substituted with 1 to 4 deuteriums, or biphenyldiyl that is unsubstituted or substituted with 1 to 8 deuteriums. More preferably, L.sub.6 and L.sub.7 can be each independently a single bond, phenylene, biphenyldiyl, or phenylene substituted with 4 deuteriums.

[0075] Preferably, Ar.sub.3 and Ar.sub.4 can be each independently a substituted or unsubstituted C.sub.6-20 aryl or a substituted or unsubstituted C.sub.2-20 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S. Preferably, Ar.sub.3 and Ar.sub.4 can be each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenyl naphthyl, phenanthrenyl, triphenylenyl, phenyl phenanthrenyl, dimethyl fluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, methyl dibenzofluorenyl, carbazolyl, or phenyl carbazolyl, wherein the Ar.sub.3 and Ar.sub.4 can be each independently unsubstituted or substituted with at least one deuterium. More preferably, Ar.sub.3 and Ar.sub.4 can be each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenyl naphthyl, phenanthrenyl, triphenylenyl, phenyl phenanthrenyl, dimethyl fluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, methyl dibenzofluorenyl, carbazolyl, phenyl carbazolyl, phenyl substituted with 5 deuteriums, biphenylyl substituted with 4 deuteriums, biphenylyl substituted with 9 deuteriums, or terphenylyl substituted with 4 deuteriums.

[0076] Preferably, each R.sub.2 can be hydrogen.

[0077] Representative examples of the compound represented by Chemical Formula 2 are as follows:

##STR00265## ##STR00266## ##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271## ##STR00272## ##STR00273## ##STR00274## ##STR00275## ##STR00276## ##STR00277## ##STR00278## ##STR00279## ##STR00280##

##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288## ##STR00289## ##STR00290## ##STR00291## ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296## ##STR00297## ##STR00298## ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313## ##STR00314## ##STR00315## ##STR00316## ##STR00317## ##STR00318## ##STR00319## ##STR00320## ##STR00321## ##STR00322## ##STR00323## ##STR00324## ##STR00325## ##STR00326## ##STR00327## ##STR00328## ##STR00329## ##STR00330## ##STR00331## ##STR00332## ##STR00333## ##STR00334## ##STR00335## ##STR00336## ##STR00337## ##STR00338## ##STR00339## ##STR00340## ##STR00341## ##STR00342## ##STR00343## ##STR00344##

##STR00345## ##STR00346## ##STR00347## ##STR00348## ##STR00349## ##STR00350## ##STR00351## ##STR00352## ##STR00353## ##STR00354## ##STR00355## ##STR00356## ##STR00357## ##STR00358## ##STR00359## ##STR00360## ##STR00361## ##STR00362## ##STR00363## ##STR00364## ##STR00365## ##STR00366## ##STR00367## ##STR00368## ##STR00369## ##STR00370## ##STR00371## ##STR00372## ##STR00373## ##STR00374## ##STR00375## ##STR00376## ##STR00377## ##STR00378## ##STR00379## ##STR00380## ##STR00381## ##STR00382## ##STR00383## ##STR00384## ##STR00385##

[0078] The compound of Chemical Formula 2 wherein A is

##STR00386##

can be prepared by a preparation method as shown in the following Reaction Scheme 2 as an example, and the other remaining compounds can be prepared in a similar manner.

##STR00387##

[0079] In Reaction Scheme 2, B, R.sub.2, a, L.sub.4 to L.sub.7, Ar.sub.3 and Ar.sub.4 are the same as defined in Reaction Formula 2, and Z.sub.3 is halogen, preferably Z.sub.3 is chloro or bromo.

[0080] Reaction Scheme 2 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and a reactive group for the amine substitution reaction can be modified as known in the art. The preparation method can be further embodied in Preparation Examples described hereinafter.

[0081] Preferably, the weight ratio of the compound of Chemical Formula 1 and the compound of Chemical Formula 2 in the light emitting layer can be 10:90 to 90:10, more preferably 20:80 to 80:20, 30:70 to 70:30 or 40:60 to 60:40.

[0082] Meanwhile, the light emitting layer can further include a dopant in addition to the host. The dopant material is not particularly limited as long as it is a material used for the organic light emitting device. As an example, an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like can be mentioned. Specific examples of the aromatic amine derivatives include substituted or unsubstituted fused aromatic ring derivatives having an arylamino group, examples thereof include pyrene, anthracene, chrysene, and periflanthene having the arylamino group, and the like. The styrylamine compound is a compound where at least one arylvinyl group is substituted in substituted or unsubstituted arylamine, in which one or two or more substituent groups selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, and the like, but are not limited thereto. Further, examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto. In one example, one or more selected from the following group can be used as a dopant material, but is not limited thereto:

##STR00388## ##STR00389## ##STR00390## ##STR00391## ##STR00392## ##STR00393## ##STR00394## ##STR00395##

Hole Blocking Layer

[0083] The organic light emitting device according to the present disclosure can include a hole blocking layer on the light emitting layer, if necessary.

[0084] The hole blocking layer is a layer provided between the electron transport layer and the light emitting layer in order to prevent the holes injected in the anode from being transferred to the electron transport layer without being recombined in the light emitting layer, which can also be referred to as a hole inhibition layer or a hole stopping layer. The hole blocking layer is preferably a material having the large ionization energy.

Electron Transport Layer

[0085] The organic light emitting device according to the present disclosure can include an electron transport layer on the light emitting layer (or the hole blocking layer), if necessary.

[0086] The electron transport layer is a layer that receives the electrons from the cathode or the electron injection layer formed on the cathode and transports the electrons to the light emitting layer, and that suppress the transfer of holes from the light emitting layer, and an electron transport material is suitably a material which can receive well injection of electrons from a cathode and transfer the electrons to a light emitting layer, and has a large mobility for electrons.

[0087] Specific examples of the electron transport material include: an Al complex of 8-hydroxyquinoline; a complex including Alq.sub.3; an organic radical compound; a hydroxyflavone-metal complex, and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used according to a conventional technique. In particular, appropriate examples of the cathode material are a typical material which has a low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium, and samarium, in each case followed by an aluminum layer or a silver layer.

Electron Injection Layer

[0088] The organic light emitting device according to the present disclosure can further include an electron injection layer on the light emitting layer (or on the electron transport layer, if the electron transport layer exists), if necessary.

[0089] The electron injection layer is a layer which injects electrons from an electrode, and is preferably a compound which has a capability of transporting electrons, has an effect of injecting electrons from a cathode and an excellent effect of injecting electrons into a light emitting layer or a light emitting material, prevents excitons produced from the light emitting layer from moving to a hole injection layer, and is also excellent in the ability to form a thin film.

[0090] Specific examples of the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, a metal complex compound, a nitrogen-containing 5-membered ring derivative, and the like, but are not limited thereto.

[0091] Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, and the like, but are not limited thereto.

Organic Light Emitting Device

[0092] The structure of the organic light emitting device according to the present disclosure is illustrated in FIGS. 1 and 2. FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4.

[0093] The organic light emitting device according to the present disclosure can be manufactured by sequentially stacking the above-described structures. In this case, the organic light emitting device can be manufactured by depositing a metal, metal oxides having conductivity, or an alloy thereof on the substrate by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method to form the anode, forming the respective layers described above thereon, and then depositing a material that can be used as the cathode thereon. In addition to such a method, the organic light emitting device can be manufactured by sequentially depositing from the cathode material to the anode material on a substrate in the reverse order of the above-mentioned configuration (WO 2003/012890). Further, the light emitting layer can be formed by subjecting hosts and dopants to a vacuum deposition method and a solution coating method. Herein, the solution coating method means a spin coating, a dip coating, a doctor blading, an inkjet printing, a screen printing, a spray method, a roll coating, or the like, but is not limited thereto.

[0094] Meanwhile, the organic light emitting device according to the present disclosure can be a bottom emission device, a top emission device, or a double-sided light emitting device, and particularly, can be a bottom emission device that requires relatively high luminous efficiency.

[0095] Below, preferable embodiments are presented to assist in the understanding of the present disclosure. The following examples are only provided for a better understanding of the present disclosure, and is not intended to limit the content of the present disclosure.

Synthesis Example 1-1

[0096] ##STR00396## ##STR00397##

[0097] Compound A (15 g, 45.5 mmol) and Compound Trz1 (15.2 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.9 g of Compound subA-1. (Yield: 63%, MS: [M+H].sup.+=485)

[0098] Compound subA-1 (15 g, 30.9 mmol) and Compound sub1 (7.2 g, 32.5 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (12.8 g, 92.8 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.6 g of Compound 1-1. (Yield: 60%, MS: [M+H].sup.+=627)

Synthesis Example 1-2

[0099] ##STR00398##

[0100] Compound B (15 g, 45.5 mmol) and Compound Trz2 (12.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.6 g of Compound subB-1. (Yield: 69%, MS: [M+H].sup.+=435)

[0101] Compound subB-1 (15 g, 34.5 mmol) and Compound sub2 (9.9 g, 36.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.5 g of Compound 1-2. (Yield: 67%, MS: [M+H].sup.+=627)

Synthesis Example 1-3

[0102] ##STR00399##

C

[0103] Compound C (15 g, 45.5 mmol) and Compound Trz2 (12.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.6 g of Compound subC-1. (Yield: 64%, MS: [M+H].sup.+=435) Compound subC-1 (15 g, 34.5 mmol) and Compound sub3 (8.9 g, 36.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed.

[0104] Then, potassium carbonate (14.3 g, 103.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.1 g of Compound 1-3. (Yield: 68%, MS: [M+H].sup.+=601)

Synthesis Example 1-4

[0105] ##STR00400## ##STR00401##

[0106] Compound D (15 g, 45.5 mmol) and Compound Trz3 (21.2 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 21.1 g of Compound subD-1. (Yield: 76%, MS: [M+H].sup.+=611)

[0107] Compound subD-1 (15 g, 24.5 mmol) and Compound sub4 (3.1 g, 25.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (10.2 g, 73.6 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.8 g of Compound 1-4. (Yield: 80%, MS: [M+H].sup.+=653)

Synthesis Example 1-5

[0108] ##STR00402##

[0109] Compound E (15 g, 50.8 mmol) and Compound Trz4 (25 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 20.4 g of Compound 1-5. (Yield: 67%, MS: [M+H].sup.+=601)

Synthesis Example 1-6

[0110] ##STR00403##

[0111] Compound E (15 g, 50.8 mmol) and Compound Trz5 (25.8 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 20.4 g of Compound 1-6. (Yield: 65%, MS: [M+H].sup.+=617)

Synthesis Example 1-7

[0112] ##STR00404##

[0113] Compound E (15 g, 50.8 mmol) and Compound Trz6 (28.5 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled.

[0114] This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 20.7 g of Compound 1-7. (Yield: 61%, MS: [M+H].sup.+=667)

Synthesis Example 1-8

[0115] ##STR00405##

[0116] Compound E (15 g, 50.8 mmol) and Compound Trz7 (26.4 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 24.2 g of Compound 1-8. (Yield: 76%, MS: [M+H].sup.+=627)

Synthesis Example 1-9

[0117] ##STR00406##

[0118] Compound F (15 g, 45.5 mmol) and Compound Trz8 (19.5 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 17 g of Compound subF-1. (Yield: 65%, MS: [M+H].sup.+=575)

[0119] Compound subF-1 (15 g, 26.1 mmol) and Compound sub4 (3.3 g, 27.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (10.8 g, 78.3 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.9 g of Compound 1-9. (Yield: 80%, MS: [M+H].sup.+=617)

Synthesis Example 1-10

[0120] ##STR00407##

[0121] Compound G (15 g, 45.5 mmol) and Compound Trz9 (20.7 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 21.9 g of Compound subG-1. (Yield: 80%, MS: [M+H].sup.+=601)

[0122] Compound subG-1 (15 g, 25 mmol) and Compound sub5 (4.5 g, 26.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (10.3 g, 74.9 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13 g of Compound 1-10. (Yield: 75%, MS: [M+H].sup.+=693)

Synthesis Example 1-11

[0123] ##STR00408##

[0124] Compound G (15 g, 45.5 mmol) and Compound Trz2 (12.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.8 g of Compound subG-2. (Yield: 70%, MS: [M+H].sup.+=435)

[0125] Compound subG-2 (15 g, 34.5 mmol) and Compound sub6 (17.5 g, 36.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14 g of Compound 1-11. (Yield: 65%, MS: [M+H].sup.+=627)

Synthesis Example 1-12

[0126] ##STR00409## ##STR00410##

[0127] Compound G (15 g, 45.5 mmol) and Compound Trz10 (16.4 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.2 g of Compound subG-3. (Yield: 61%, MS: [M+H].sup.+=511)

[0128] Compound subG-3 (10 g, 19.6 mmol), Compound sub7 (4.3 g, 20 mmol), and sodium tert-butoxide (2.4 g, 25.4 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 9.5 g of Compound 1-12. (Yield: 70%, MS: [M+H].sup.+=692)

Synthesis Example 1-13

[0129] ##STR00411## ##STR00412##

[0130] Compound H (15 g, 45.5 mmol) and Compound Trz11 (17.1 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 16.2 g of Compound subH-1. (Yield: 68%, MS: [M+H].sup.+=525)

[0131] Compound subH-1 (15 g, 28.6 mmol) and Compound sub5 (5.2 g, 30 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (11.8 g, 85.7 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 10.9 g of Compound 1-13. (Yield: 62%, MS: [M+H].sup.+=617)

Synthesis Example 1-14

[0132] ##STR00413##

[0133] Compound I (15 g, 50.8 mmol) and Compound Trz12 (23.7 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 17.6 g of Compound 1-14. (Yield: 60%, MS: [M+H].sup.+=577)

Synthesis Example 1-15

[0134] ##STR00414##

[0135] Compound I (15 g, 50.8 mmol) and Compound Trz13 (25 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 21.7 g of Compound 1-15. (Yield: 71%, MS: [M+H].sup.+=601)

Synthesis Example 1-16

[0136] ##STR00415##

[0137] Compound I (15 g, 50.8 mmol) and Compound Trz14 (25.1 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 21.4 g of Compound 1-16. (Yield: 70%, MS: [M+H].sup.+=603)

Synthesis Example 1-17

[0138] ##STR00416##

[0139] Compound J (15 g, 45.5 mmol) and Compound Trz15 (17.6 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 15.6 g of Compound subJ-1. (Yield: 64%, MS: [M+H].sup.+=535)

[0140] Compound subJ-1 (15 g, 28 mmol) and Compound sub5 (5.1 g, 29.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (11.6 g, 84.1 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.7 g of Compound 1-17. (Yield: 78%, MS: [M+H].sup.+=627)

Synthesis Example 1-18

[0141] ##STR00417##

[0142] Compound K (15 g, 45.5 mmol) and Compound Trz1 (15.2 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.9 g of Compound subK-1. (Yield: 63%, MS: [M+H].sup.+=485)

[0143] Compound subK-1 (15 g, 30.9 mmol) and Compound sub8 (6.9 g, 32.5 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (12.8 g, 92.8 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.4 g of Compound 1-18. (Yield: 65%, MS: [M+H].sup.+=617)

Synthesis Example 1-19

[0144] ##STR00418##

[0145] Compound L (15 g, 45.5 mmol) and Compound Trz2 (12.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.6 g of Compound subL-1. (Yield: 69%, MS: [M+H].sup.+=435)

[0146] Compound subL-1 (15 g, 34.5 mmol) and Compound sub9 (8.9 g, 36.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.2 g of Compound 1-19. (Yield: 64%, MS: [M+H].sup.+=601)

Synthesis Example 1-20

[0147] ##STR00419##

[0148] Compound subL-1 (15 g, 34.5 mmol) and Compound sub10 (10.1 g, 36.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.4 g of Compound 1-20. (Yield: 66%, MS: [M+H].sup.+=633)

Synthesis Example 1-21

[0149] ##STR00420## ##STR00421##

[0150] Compound K (15 g, 45.5 mmol) and Compound Trz16 (17.9 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 16.7 g of Compound subK-2. (Yield: 68%, MS: [M+H].sup.+=541)

[0151] Compound subK-2 (10 g, 18.5 mmol), Compound sub11 (3.2 g, 18.9 mmol), and sodium tert-butoxide (2.3 g, 24 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 7.8 g of Compound 1-21. (Yield: 63%, MS: [M+H].sup.+=672)

Synthesis Example 1-22

[0152] ##STR00422## ##STR00423##

[0153] Compound K (15 g, 45.5 mmol) and Compound Trz17 (16.4 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 15.3 g of Compound subK-3. (Yield: 66%, MS: [M+H].sup.+=511)

[0154] Compound subK-3 (15 g, 29.4 mmol) and Compound sub5 (5.3 g, 30.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (12.2 g, 88.1 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.8 g of Compound 1-22. (Yield: 78%, MS: [M+H].sup.+=603)

Synthesis Example 1-23

[0155] ##STR00424##

[0156] Compound M (15 g, 50.8 mmol) and Compound Trz18 (25.1 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 19.9 g of Compound 1-23. (Yield: 65%, MS: [M+H].sup.+=603)

Synthesis Example 1-24

[0157] ##STR00425##

[0158] Compound M (15 g, 50.8 mmol) and Compound Trz19 (25 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 20.4 g of Compound 1-24. (Yield: 67%, MS: [M+H].sup.+=601)

Synthesis Example 1-25

[0159] ##STR00426##

[0160] Compound M (15 g, 50.8 mmol) and Compound Trz20 (25.8 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 19.7 g of Compound 1-25. (Yield: 63%, MS: [M+H].sup.+=617)

Synthesis Example 1-26

[0161] ##STR00427## ##STR00428##

[0162] Compound N (15 g, 45.5 mmol) and Compound Trz1 (15.2 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 15.9 g of Compound subN-1. (Yield: 72%, MS: [M+H].sup.+=485)

[0163] Compound subN-1 (15 g, 30.9 mmol) and Compound sub5 (5.6 g, 32.5 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (12.8 g, 92.8 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.7 g of Compound 1-26. (Yield: 71%, MS: [M+H].sup.+=577)

Synthesis Example 1-27

[0164] ##STR00429##

[0165] Compound O (15 g, 45.5 mmol) and Compound Trz2 (12.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 15 g of Compound subO-1. (Yield: 76%, MS: [M+H].sup.+=435)

[0166] Compound subO-1 (15 g, 34.5 mmol) and Compound sub12 (9.9 g, 36.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 15.8 g of Compound 1-27. (Yield: 73%, MS: [M+H].sup.+=627)

Synthesis Example 1-28

[0167] ##STR00430##

[0168] Compound N (15 g, 45.5 mmol) and Compound Trz8 (12.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 20.4 g of Compound subN-2. (Yield: 78%, MS: [M+H].sup.+=575)

[0169] Compound subN-2 (15 g, 26.1 mmol) and Compound sub13 (5.4 g, 27.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (10.8 g, 78.3 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 10.8 g of Compound 1-28. (Yield: 60%, MS: [M+H].sup.+=693)

Synthesis Example 1-29

[0170] ##STR00431##

[0171] Compound P (15 g, 45.5 mmol) and Compound Trz1 (15.2 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.7 g of Compound subP-1. (Yield: 62%, MS: [M+H].sup.+=485)

[0172] Compound subP-1 (10 g, 20.6 mmol), Compound sub11 (3.5 g, 21 mmol), and sodium tert-butoxide (2.6 g, 26.8 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 4 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 6.5 g of Compound 1-29. (Yield: 51%, MS: [M+H].sup.+=616)

Synthesis Example 1-30

[0173] ##STR00432##

[0174] Compound Q (15 g, 45.5 mmol) and Compound Trz21 (17.1 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 16.5 g of Compound subQ-1. (Yield: 69%, MS: [M+H].sup.+=525)

[0175] Compound subQ-1 (15 g, 28.6 mmol) and Compound sub14 (5.9 g, 30 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (11.8 g, 85.7 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.7 g of Compound 1-30. (Yield: 80%, MS: [M+H].sup.+=643)

Synthesis Example 1-31

[0176] ##STR00433##

[0177] Compound R (15 g, 50.8 mmol) and Compound Trz22 (23.7 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 18.7 g of Compound 1-31. (Yield: 64%, MS: [M+H].sup.+=577)

Synthesis Example 1-32

[0178] ##STR00434##

[0179] Compound R (15 g, 50.8 mmol) and Compound Trz23 (23.6 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 23.1 g of Compound 1-32. (Yield: 79%, MS: [M+H].sup.+=575)

Synthesis Example 1-33

[0180] ##STR00435##

[0181] Compound R (15 g, 50.8 mmol) and Compound Trz24 (29.9 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 26 g of Compound 1-33. (Yield: 74%, MS: [M+H].sup.+=693)

Synthesis Example 1-34

[0182] ##STR00436##

[0183] Compound S (15 g, 45.5 mmol) and Compound Trz15 (17.6 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 19 g of Compound subS-1. (Yield: 78%, MS: [M+H].sup.+=535)

[0184] Compound subS-1 (15 g, 28 mmol) and Compound sub15 (6.5 g, 29.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (11.6 g, 84.1 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.3 g of Compound 1-34. (Yield: 70%, MS: [M+H].sup.+=677)

Synthesis Example 1-35

[0185] ##STR00437##

[0186] Compound T (15 g, 45.5 mmol) and Compound Trz2 (12.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.4 g of Compound subT-1. (Yield: 73%, MS: [M+H].sup.+=435)

[0187] Compound subT-1 (15 g, 34.5 mmol) and Compound sub16 (9.5 g, 36.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 17 g of Compound 1-35. (Yield: 80%, MS: [M+H].sup.+=617)

Synthesis Example 1-36

[0188] ##STR00438##

[0189] Compound S (15 g, 45.5 mmol) and Compound Trz25 (18.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 19.6 g of Compound subS-2. (Yield: 77%, MS: [M+H].sup.+=561)

[0190] Compound subS-2 (10 g, 17.8 mmol), Compound sub17 (4 g, 18.2 mmol), and sodium tert-butoxide (2.2 g, 23.2 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 7.3 g of Compound 1-36. (Yield: 55%, MS: [M+H].sup.+=742)

Synthesis Example 1-37

[0191] ##STR00439##

[0192] Compound U (15 g, 45.5 mmol) and Compound Trz26 (17.9 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 18.7 g of Compound subU-1. (Yield: 76%, MS: [M+H].sup.+=541)

[0193] Compound subU-1 (15 g, 27.7 mmol) and Compound sub18 (6.6 g, 29.1 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (11.5 g, 83.2 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.5 g of Compound 1-37. (Yield: 71%, MS: [M+H].sup.+=689)

Synthesis Example 1-38

[0194] ##STR00440##

[0195] Compound V (15 g, 50.8 mmol) and Compound Trz27 (22.3 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 16.8 g of Compound 1-38. (Yield: 60%, MS: [M+H].sup.+=551)

Synthesis Example 1-39

[0196] ##STR00441##

[0197] Compound V (15 g, 50.8 mmol) and Compound Trz28 (23.2 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 20.1 g of Compound 1-39. (Yield: 70%, MS: [M+H].sup.+=567)

Synthesis Example 1-40

[0198] ##STR00442##

[0199] Compound V (15 g, 50.8 mmol) and Compound Trz29 (30.4 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 24.6 g of Compound 1-40. (Yield: 69%, MS: [M+H].sup.+=703)

Synthesis Example 1-41

[0200] ##STR00443##

[0201] Compound V (15 g, 50.8 mmol) and Compound Trz30 (25.8 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 23.8 g of Compound 1-41. (Yield: 76%, MS: [M+H].sup.+=617)

Synthesis Example 1-42

[0202] ##STR00444##

[0203] Compound W (15 g, 45.5 mmol) and Compound Trz2 (12.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13 g of Compound subW-1. (Yield: 66%, MS: [M+H].sup.+=435)

[0204] Compound subW-1 (15 g, 34.5 mmol) and Compound sub19 (9.9 g, 36.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 16.4 g of Compound 1-42. (Yield: 76%, MS: [M+H].sup.+=627)

Synthesis Example 1-43

[0205] ##STR00445##

[0206] Compound X (15 g, 45.5 mmol) and Compound Trz2 (12.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14 g of Compound subX-1. (Yield: 71%, MS: [M+H].sup.+=435)

[0207] Compound subX-1 (15 g, 34.5 mmol) and Compound sub20 (10.1 g, 36.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14 g of Compound 1-43. (Yield: 64%, MS: [M+H].sup.+=633)

Synthesis Example 1-44

[0208] ##STR00446##

[0209] Compound Y (15 g, 45.5 mmol) and Compound Trz2 (12.6 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 15.8 g of Compound subY-1. (Yield: 80%, MS: [M+H].sup.+=435)

[0210] Compound subY-1 (15 g, 34.5 mmol) and Compound sub21 (9.5 g, 36.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.9 g of Compound 1-44. (Yield: 70%, MS: [M+H].sup.+=617)

Synthesis Example 1-45

[0211] ##STR00447##

[0212] Compound X (15 g, 45.5 mmol) and Compound Trz31 (18.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 18.1 g of Compound subX-2. (Yield: 71%, MS: [M+H].sup.+=561)

[0213] Compound subX-2 (15 g, 26.7 mmol) and Compound sub22 (7.6 g, 28.1 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (11.1 g, 80.2 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 15.7 g of Compound 1-45. (Yield: 78%, MS: [M+H].sup.+=753)

Synthesis Example 1-46

[0214] ##STR00448##

[0215] Compound Z (15 g, 50.8 mmol) and Compound Trz32 (21 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 16.6 g of Compound 1-46. (Yield: 62%, MS: [M+H].sup.+=527)

Synthesis Example 1-47

[0216] ##STR00449##

[0217] Compound Z (15 g, 50.8 mmol) and Compound Trz33 (22.3 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 19.3 g of Compound 1-47. (Yield: 69%, MS: [M+H].sup.+=551)

Synthesis Example 1-48

[0218] ##STR00450##

[0219] Compound Z (15 g, 50.8 mmol) and Compound Trz34 (25.7 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 23.1 g of Compound 1-48. (Yield: 74%, MS: [M+H].sup.+=615)

Synthesis Example 1-49

[0220] ##STR00451##

[0221] Compound Z (15 g, 50.8 mmol) and Compound Trz35 (25.8 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 22.9 g of Compound 1-49. (Yield: 73%, MS: [M+H].sup.+=617)

Synthesis Example 1-50

[0222] ##STR00452##

[0223] Compound Z (15 g, 50.8 mmol) and Compound Trz36 (25.8 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 19.4 g of Compound 1-50. (Yield: 62%, MS: [M+H].sup.+=617)

Synthesis Example 1-51

[0224] ##STR00453##

[0225] Compound Z (15 g, 50.8 mmol) and Compound Trz37 (27.8 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 19.9 g of Compound 1-51. (Yield: 60%, MS: [M+H].sup.+=653)

Synthesis Example 1-52

[0226] ##STR00454##

[0227] Compound AA (15 g, 45.5 mmol) and Compound Trz1 (15.2 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 17.2 g of Compound subAA-1. (Yield: 78%, MS: [M+H].sup.+=485)

[0228] Compound subAA-1 (15 g, 30.9 mmol) and Compound sub23 (7.4 g, 32.5 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (12.8 g, 92.8 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.9 g of Compound 1-52. (Yield: 71%, MS: [M+H].sup.+=633)

Synthesis Example 1-53

[0229] ##STR00455##

[0230] Compound AB (15 g, 45.5 mmol) and Compound Trz2 (12.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14 g of Compound subAB-1. (Yield: 71%, MS: [M+H].sup.+=435)

[0231] Compound subAB-1 (14 g, 32 mmol) and Compound sub24 (8.9 g, 33.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (13.3 g, 96.6 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.5 g of Compound 1-53. (Yield: 62%, MS: [M+H].sup.+=617)

Synthesis Example 1-54

[0232] ##STR00456##

[0233] Compound AA (15 g, 45.5 mmol) and Compound Trz2 (12.8 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.6 g of Compound subAA-2. (Yield: 64%, MS: [M+H].sup.+=435)

[0234] Compound subAA-2 (15 g, 34.5 mmol) and Compound sub25 (10.1 g, 36.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.3 g of Compound 1-54. (Yield: 61%, MS: [M+H].sup.+=633)

Synthesis Example 1-55

[0235] ##STR00457##

[0236] Compound AB (15 g, 45.5 mmol) and Compound Trz21 (17.1 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 15.5 g of Compound subAB-2. (Yield: 65%, MS: [M+H].sup.+=525)

[0237] Compound subAB-2 (15 g, 28.6 mmol) and Compound sub26 (7.4 g, 30 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (11.8 g, 85.7 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.5 g of Compound 1-55. (Yield: 63%, MS: [M+H].sup.+=693)

Synthesis Example 1-56

[0238] ##STR00458##

[0239] Compound AB (15 g, 45.5 mmol) and Compound Trz38 (20.1 g, 47.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 18.4 g of Compound subAB-3. (Yield: 69%, MS: [M+H].sup.+=587)

[0240] Compound subAB-3 (15 g, 25.6 mmol) and Compound sub27 (5.7 g, 26.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (10.6 g, 76.7 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.4 g of Compound 1-56. (Yield: 73%, MS: [M+H].sup.+=719)

Synthesis Example 1-57

[0241] ##STR00459##

[0242] Compound AC (15 g, 50.8 mmol) and Compound Trz39 (22.3 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 22.1 g of Compound 1-57. (Yield: 79%, MS: [M+H].sup.+=551)

Synthesis Example 1-58

[0243] ##STR00460##

[0244] Compound AC (15 g, 50.8 mmol) and Compound Trz40 (23.7 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 19.3 g of Compound 1-58. (Yield: 66%, MS: [M+H].sup.+=577)

Synthesis Example 1-59

[0245] ##STR00461##

[0246] Compound AC (15 g, 50.8 mmol) and Compound Trz41 (28.5 g, 53.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 152.5 mmol) was dissolved in 100 ml of water and added thereto, and the mixture was sufficiently stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 24.7 g of Compound 1-59. (Yield: 73%, MS: [M+H].sup.+=667)

Synthesis Example 2-1

[0247] ##STR00462##

[0248] Compound 2-A (15 g, 58.3 mmol) and Compound 2-B (10 g, 64.2 mmol) were added to 300 ml of THE under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (16.1 g, 116.7 mmol) was dissolved in 48 ml of water and added thereto, and the mixture was sufficiently stirred and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.6 g of Compound sub2-A-1. (Yield: 75%, MS: [M+H].sup.+=289)

[0249] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-1 (12.9 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.7 g of Compound 2-1. (Yield: 59%, MS: [M+H].sup.+=624)

Synthesis Example 2-2

[0250] ##STR00463##

[0251] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-2 (11.1 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 10.1 g of Compound 2-2. (Yield: 51%, MS: [M+H].sup.+=574)

Synthesis Example 2-3

[0252] ##STR00464##

[0253] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-3 (14.3 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.2 g of Compound 2-3. (Yield: 53%, MS: [M+H].sup.+=664)

Synthesis Example 2-4

[0254] ##STR00465##

[0255] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-4 (13.9 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14 g of Compound 2-4. (Yield: 62%, MS: [M+H].sup.+=654)

Synthesis Example 2-5

[0256] ##STR00466##

[0257] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-5 (13.8 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.2 g of Compound 2-5. (Yield: 50%, MS: [M+H].sup.+=650)

Synthesis Example 2-6

[0258] ##STR00467##

[0259] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-6 (14.8 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.2 g of Compound 2-6. (Yield: 52%, MS: [M+H].sup.+=680)

Synthesis Example 2-7

[0260] ##STR00468##

[0261] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-7 (12.2 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 1 g of Compound 2-7. (Yield: 50%, MS: [M+H].sup.+=61)

Synthesis Example 2-8

[0262] ##STR00469##

[0263] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-8 (13.9 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.3 g of Compound 2-8. (Yield: 59%, MS: [M+H].sup.+=654)

Synthesis Example 2-9

[0264] ##STR00470##

[0265] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-9 (9.3 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.2 g of Compound 2-9. (Yield: 62%, MS: [M+H].sup.+=522)

Synthesis Example 2-10

[0266] ##STR00471##

[0267] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-10 (14.5 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.4 g of Compound 2-10. (Yield: 62%, MS: [M+H].sup.+=672)

Synthesis Example 2-11

[0268] ##STR00472##

[0269] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-11 (13.4 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.4 g of Compound 2-11. (Yield: 56%, MS: [M+H].sup.+=638)

Synthesis Example 2-12

[0270] ##STR00473##

[0271] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-12 (12 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11 g of Compound 2-12. (Yield: 53%, MS: [M+H].sup.+=598)

Synthesis Example 2-13

[0272] ##STR00474##

[0273] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-13 (14.3 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 15.6 g of Compound 2-13. (Yield: 68%, MS: [M+H].sup.+=664)

Synthesis Example 2-14

[0274] ##STR00475##

[0275] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-14 (13.3 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.2 g of Compound 2-14. (Yield: 60%, MS: [M+H].sup.+=638)

Synthesis Example 2-15

[0276] ##STR00476##

[0277] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-15 (13.9 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12 g of Compound 2-15. (Yield: 53%, MS: [M+H].sup.+=654)

Synthesis Example 2-16

[0278] ##STR00477##

[0279] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-16 (12.7 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.7 g of Compound 2-16. (Yield: 64%, MS: [M+H].sup.+=618)

Synthesis Example 2-17

[0280] ##STR00478##

[0281] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-17 (12.1 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.5 g of Compound 2-17. (Yield: 55%, MS: [M+H].sup.+=602)

Synthesis Example 2-18

[0282] ##STR00479##

[0283] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-18 (12.1 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.4 g of Compound 2-18. (Yield: 69%, MS: [M+H].sup.+=602)

Synthesis Example 2-19

[0284] ##STR00480##

[0285] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-19 (13.2 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.4 g of Compound 2-19. (Yield: 52%, MS: [M+H].sup.+=634)

Synthesis Example 2-20

[0286] ##STR00481##

[0287] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-20 (12.5 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.2 g of Compound 2-20. (Yield: 62%, MS: [M+H].sup.+=614)

Synthesis Example 2-21

[0288] ##STR00482##

[0289] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-21 (14.3 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.2 g of Compound 2-21. (Yield: 62%, MS: [M+H].sup.+=664)

Synthesis Example 2-22

[0290] ##STR00483##

[0291] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-22 (12 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.2 g of Compound 2-22. (Yield: 54%, MS: [M+H].sup.+=598)

Synthesis Example 2-23

[0292] ##STR00484##

[0293] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-23 (11.1 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.9 g of Compound 2-23. (Yield: 60%, MS: [M+H].sup.+=572)

Synthesis Example 2-24

[0294] ##STR00485##

[0295] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-24 (12.9 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.6 g of Compound 2-24. (Yield: 63%, MS: [M+H].sup.+=624)

Synthesis Example 2-25

[0296] ##STR00486##

[0297] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-25 (13.3 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(O) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.3 g of Compound 2-25. (Yield: 65%, MS: [M+H].sup.+=638)

Synthesis Example 2-26

[0298] ##STR00487##

[0299] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-26 (12.5 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(O) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 10.8 g of Compound 2-26. (Yield: 51%, MS: [M+H].sup.+=614)

Synthesis Example 2-27

[0300] ##STR00488##

[0301] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-27 (14.6 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 16.1 g of Compound 2-27. (Yield: 69%, MS: [M+H].sup.+=674)

Synthesis Example 2-28

[0302] ##STR00489##

[0303] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-28 (13.8 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.2 g of Compound 2-28. (Yield: 50%, MS: [M+H].sup.+=650)

Synthesis Example 2-29

[0304] ##STR00490##

[0305] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-29 (16.4 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 17.1 g of Compound 2-29. (Yield: 68%, MS: [M+H].sup.+=726)

Synthesis Example 2-30

[0306] ##STR00491##

[0307] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-30 (13.8 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.4 g of Compound 2-30. (Yield: 64%, MS: [M+H].sup.+=650)

Synthesis Example 2-31

[0308] ##STR00492##

[0309] Compound 2-A (15 g, 58.3 mmol) and Compound 2-C (10 g, 64.2 mmol) were added to 300 ml of THE under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (16.1 g, 116.7 mmol) was dissolved in 48 ml of water and added thereto, and the mixture was sufficiently stirred and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 10.6 g of Compound sub2-A-2. (Yield: 63%, MS: [M+H].sup.+=289)

[0310] Compound sub2-A-2 (10 g, 34.6 mmol), Compound sub2-31 (15.1 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 16.7 g of Compound 2-31. (Yield: 70%, MS: [M+H].sup.+=688)

Synthesis Example 2-32

[0311] ##STR00493##

[0312] Compound sub2-A-2 (10 g, 34.6 mmol), Compound sub2-32 (17.7 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 16.6 g of Compound 2-32. (Yield: 63%, MS: [M+H].sup.+=763)

Synthesis Example 2-33

[0313] ##STR00494##

[0314] Compound sub2-A-2 (10 g, 34.6 mmol), Compound sub2-33 (14.6 g, 34.6 mmol), and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.6 g of Compound 2-33. (Yield: 54%, MS: [M+H].sup.+=674)

Synthesis Example 2-34

[0315] ##STR00495##

[0316] Compound 2-A (15 g, 58.3 mmol) and Compound 2-D (14.9 g, 64.2 mmol) were added to 300 ml of THE under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (16.1 g, 116.7 mmol) was dissolved in 48 ml of water and added thereto, and the mixture was sufficiently stirred and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 16.8 g of Compound sub2-A-3. (Yield: 79%, MS: [M+H].sup.+=365)

[0317] Compound sub2-A-3 (10 g, 27.4 mmol), Compound sub2-34 (8.8 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.2 g of Compound 2-34. (Yield: 63%, MS: [M+H].sup.+=650)

Synthesis Example 2-35

[0318] ##STR00496##

[0319] Compound sub2-A-3 (10 g, 27.4 mmol), Compound sub2-35 (8.1 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 8.7 g of Compound 2-35. (Yield: 51%, MS: [M+H].sup.+=624)

Synthesis Example 2-36

[0320] ##STR00497##

[0321] Compound sub2-A-3 (10 g, 27.4 mmol), Compound sub2-36 (9.6 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.1 g of Compound 2-36. (Yield: 65%, MS: [M+H].sup.+=680)

Synthesis Example 2-37

[0322] ##STR00498##

[0323] Compound 2-A (15 g, 58.3 mmol) and Compound 2-E (14.9 g, 64.2 mmol) were added to 300 ml of THE under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (16.1 g, 116.7 mmol) was dissolved in 48 ml of water and added thereto, and the mixture was sufficiently stirred and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.2 g of Compound sub2-A-4. (Yield: 67%, MS: [M+H].sup.+=365)

[0324] Compound sub2-A-4 (10 g, 27.4 mmol), Compound sub2-37 (10.9 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.9 g of Compound 2-37. (Yield: 70%, MS: [M+H].sup.+=726)

Synthesis Example 2-38

[0325] ##STR00499##

[0326] Compound sub2-A-4 (10 g, 27.4 mmol), Compound sub2-38 (10.2 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 10.7 g of Compound 2-38. (Yield: 56%, MS: [M+H].sup.+=700)

Synthesis Example 2-39

[0327] ##STR00500##

[0328] Compound sub2-A-4 (10 g, 27.4 mmol), Compound sub2-39 (10 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.8 g of Compound 2-39. (Yield: 62%, MS: [M+H].sup.+=694)

Synthesis Example 2-40

[0329] ##STR00501##

[0330] Compound 2-A (15 g, 58.3 mmol) and Compound 2-F (14.9 g, 64.2 mmol) were added to 300 ml of THE under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (16.1 g, 116.7 mmol) was dissolved in 48 ml of water and added thereto, and the mixture was sufficiently stirred and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After reacting for 8 hours, the reaction mixture was cooled to room temperature, then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.4 g of Compound sub2-A-5. (Yield: 68%, MS: [M+H].sup.+=365)

[0331] Compound sub2-A-5 (10 g, 27.4 mmol), Compound sub2-40 (10.2 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 10.7 g of Compound 2-40. (Yield: 56%, MS: [M+H].sup.+=700)

Synthesis Example 2-41

[0332] ##STR00502##

[0333] Compound sub2-A-5 (10 g, 27.4 mmol), Compound sub2-41 (10.2 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 9.8 g of Compound 2-41. (Yield: 51%, MS: [M+H].sup.+=700)

Synthesis Example 2-42

[0334] ##STR00503##

[0335] Compound sub2-A-5 (10 g, 27.4 mmol), Compound sub2-42 (11.3 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.5 g of Compound 2-42. (Yield: 57%, MS: [M+H].sup.+=740)

Synthesis Example 2-43

[0336] ##STR00504##

[0337] Compound 2-A (15 g, 58.3 mmol) and Compound 2-G (14.9 g, 64.2 mmol) were added to 300 ml of THE under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (16.1 g, 116.7 mmol) was dissolved in 48 ml of water and added thereto, and the mixture was sufficiently stirred and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After reacting for 9 hours, the reaction mixture was cooled to room temperature, then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 14.7 g of Compound sub2-A-6. (Yield: 69%, MS: [M+H].sup.+=365)

[0338] Compound sub2-A-6 (10 g, 27.4 mmol), Compound sub2-43 (8.1 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 9.7 g of Compound 2-43. (Yield: 57%, MS: [M+H].sup.+=624)

Synthesis Example 2-44

[0339] ##STR00505##

[0340] Compound sub2-A-6 (10 g, 27.4 mmol), Compound sub2-44 (11.7 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12 g of Compound 2-44. (Yield: 58%, MS: [M+H].sup.+=756)

Synthesis Example 2-45

[0341] ##STR00506##

[0342] Compound sub45 (10 g, 70.3 mmol), Compound sub2-A-2 (42.6 g, 147.7 mmol), and sodium tert-butoxide (31.0 g, 322.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (1.5 g, 2.9 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 31 g of Compound 2-45. (Yield: 68%, MS: [M+H].sup.+=648)

Synthesis Example 2-46

[0343] ##STR00507##

[0344] Compound sub46 (10 g, 59.1 mmol), Compound sub2-A-2 (35.8 g, 124.1 mmol), and sodium tert-butoxide (14.2 g, 147.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 26.7 g of Compound 2-46. (Yield: 67%, MS: [M+H].sup.+=674)

Synthesis Example 2-47

[0345] ##STR00508##

[0346] Compound sub47 (10 g, 38.6 mmol), Compound sub2-A-2 (23.4 g, 81 mmol), and sodium tert-butoxide (9.3 g, 96.4 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 15 g of Compound 2-47. (Yield: 51%, MS: [M+H].sup.+=764)

Synthesis Example 2-48

[0347] ##STR00509##

[0348] Compound sub2-A-6 (10 g, 27.4 mmol), Compound sub48 (6 g, 27.4 mmol), and sodium tert-butoxide (2.9 g, 30.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 9 g of Compound sub2-B-1. (Yield: 60%, MS: [M+H].sup.+=548)

[0349] Compound sub2-B-1 (10 g, 18.3 mmol), Compound sub2-A-1 (5.3 g, 18.3 mmol), and sodium tert-butoxide (2.3 g, 23.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 7.7 g of Compound 2-46. (Yield: 53%, MS: [M+H].sup.+=800)

Synthesis Example 2-49

[0350] ##STR00510##

[0351] Compound sub49 (10 g, 59.1 mmol), Compound sub2-A-1 (35.8 g, 124.1 mmol), and sodium tert-butoxide (14.2 g, 147.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 22.7 g of Compound 2-49. (Yield: 57%, MS: [M+H].sup.+=674)

Synthesis Example 2-50

[0352] ##STR00511##

[0353] Compound sub50 (10 g, 47.8 mmol), Compound sub2-A-1 (29 g, 100.3 mmol), and sodium tert-butoxide (11.5 g, 119.5 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 23.9 g of Compound 2-50. (Yield: 70%, MS: [M+H].sup.+=714) Synthesis Example 2-51

##STR00512##

[0354] Compound sub51 (10 g, 38.7 mmol), Compound sub2-A-1 (23.5 g, 81.3 mmol), and sodium tert-butoxide (9.3 g, 96.8 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 16.8 g of Compound 2-51. (Yield: 57%, MS: [M+H].sup.+=763)

Synthesis Example 2-52

[0355] ##STR00513##

[0356] Compound sub2-A-6 (10 g, 27.4 mmol), Compound sub46 (4.6 g, 27.4 mmol), and sodium tert-butoxide (2.9 g, 30.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 9.4 g of Compound sub2-B-2. (Yield: 69%, MS: [M+H].sup.+=498)

[0357] Compound sub2-B-2 (10 g, 20.1 mmol), Compound sub2-A-1 (5.8 g, 20.1 mmol), and sodium tert-butoxide (2.5 g, 26.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 8.3 g of Compound 2-52. (Yield: 55%, MS: [M+H].sup.+=750)

Synthesis Example 2-53

[0358] ##STR00514##

[0359] Compound sub2-A-6 (10 g, 27.4 mmol), Compound sub52 (2.6 g, 27.4 mmol), and sodium tert-butoxide (2.9 g, 30.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 5.9 g of Compound sub2-B-3. (Yield: 51%, MS: [M+H].sup.+=422)

[0360] Compound sub2-B-3 (10 g, 23.7 mmol), Compound sub2-A-1 (6.9 g, 23.7 mmol), and sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 9.3 g of Compound 2-53. (Yield: 58%, MS: [M+H].sup.+=674)

Synthesis Example 2-54

[0361] ##STR00515##

[0362] Compound sub2-A-2 (10 g, 34.6 mmol), Compound sub53 (8.5 g, 34.6 mmol), and sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.5 g of Compound sub2-B-4. (Yield: 67%, MS: [M+H].sup.+=498)

[0363] Compound sub2-B-4 (10 g, 20.1 mmol), Compound sub2-A-1 (5.8 g, 20.1 mmol), and sodium tert-butoxide (2.5 g, 26.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 7.5 g of Compound 2-54. (Yield: 50%, MS: [M+H].sup.+=750)

Synthesis Example 2-55

[0364] ##STR00516##

[0365] Compound sub2-A-2 (10 g, 34.6 mmol), Compound sub45 (5 g, 34.6 mmol), and sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 9.3 g of Compound sub2-B-5. (Yield: 68%, MS: [M+H].sup.+=396)

[0366] Compound sub2-B-5 (10 g, 25.3 mmol), Compound sub2-A-1 (7.3 g, 25.3 mmol), and sodium tert-butoxide (3.2 g, 32.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 10 g of Compound 2-55. (Yield: 61%, MS: [M+H].sup.+=648)

Synthesis Example 2-56

[0367] ##STR00517##

[0368] Compound sub2-A-2 (10 g, 34.6 mmol), Compound sub54 (6.7 g, 34.6 mmol), and sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 8.6 g of Compound sub2-B-6. (Yield: 56%, MS: [M+H].sup.+=446)

[0369] Compound sub2-B-6 (10 g, 22.4 mmol), Compound sub2-A-1 (6.5 g, 22.4 mmol), and sodium tert-butoxide (2.8 g, 29.2 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 8.8 g of Compound 2-56. (Yield: 56%, MS: [M+H].sup.+=698)

Synthesis Example 2-57

[0370] ##STR00518## ##STR00519##

[0371] Compound sub2-A-2 (10 g, 34.6 mmol), Compound sub55 (11.5 g, 34.6 mmol), and sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.2 g of Compound sub2-B-7. (Yield: 65%, MS: [M+H].sup.+=586)

[0372] Compound sub2-B-7 (10 g, 17.1 mmol), Compound sub2-A-1 (4.9 g, 17.1 mmol), and sodium tert-butoxide (2.1 g, 22.2 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 7.7 g of Compound 2-57. (Yield: 54%, MS: [M+H].sup.+=838)

Synthesis Example 2-58

[0373] ##STR00520##

[0374] Compound sub2-A-2 (10 g, 34.6 mmol), Compound sub51 (8.9 g, 34.6 mmol), and sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 10.8 g of Compound sub2-B-8. (Yield: 61%, MS: [M+H].sup.+=511)

[0375] Compound sub2-B-8 (10 g, 19.6 mmol), Compound sub2-A-1 (5.7 g, 19.6 mmol), and sodium tert-butoxide (2.4 g, 25.5 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 7.6 g of Compound 2-58. (Yield: 51%, MS: [M+H].sup.+=763)

Synthesis Example 2-59

[0376] ##STR00521##

[0377] Compound sub2-A-6 (10 g, 27.4 mmol), Compound sub56 (5.5 g, 27.4 mmol), and sodium tert-butoxide (2.9 g, 30.2 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 7.5 g of Compound sub2-B-9. (Yield: 52%, MS: [M+H].sup.+=528)

[0378] Compound sub2-B-9 (10 g, 19 mmol), Compound sub2-A-1 (5.5 g, 19 mmol), and sodium tert-butoxide (2.4 g, 24.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 8.7 g of Compound 2-59. (Yield: 59%, MS: [M+H].sup.+=780)

Synthesis Example 2-60

[0379] ##STR00522##

[0380] Compound 2-H (15 g, 45 mmol) and Compound 2-B (7.7 g, 49.5 mmol) were added to 300 ml of THE under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (12.4 g, 90 mmol) was dissolved in 37 ml of water and added thereto, and the mixture was sufficiently stirred and then tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.3 g of Compound sub2-C-1. (Yield: 75%, MS: [M+H].sup.+=365)

[0381] Compound sub2-C-1 (10 g, 27.4 mmol), Compound sub2-57 (9.5 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.7 g of Compound 2-60. (Yield: 69%, MS: [M+H].sup.+=674)

Synthesis Example 2-61

[0382] ##STR00523##

[0383] Compound sub2-C-1 (10 g, 27.4 mmol), Compound sub2-32 (14 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.6 g of Compound 2-61. (Yield: 55%, MS: [M+H].sup.+=839)

Synthesis Example 2-62

[0384] ##STR00524##

[0385] Compound sub2-C-1 (10 g, 27.4 mmol), Compound sub2-58 (10.3 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.5 g of Compound 2-62. (Yield: 65%, MS: [M+H].sup.+=704)

Synthesis Example 2-63

[0386] ##STR00525##

[0387] Compound 2-H (15 g, 45 mmol) and Compound 2-C (7.7 g, 49.5 mmol) were added to 300 ml of THE under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (12.4 g, 90 mmol) was dissolved in 37 ml of water and added thereto, and the mixture was sufficiently stirred and then tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.3 g of Compound sub2-C-2. (Yield: 75%, MS: [M+H].sup.+=365)

[0388] Compound sub2-C-2 (10 g, 27.4 mmol), Compound sub2-59 (10.3 g, 27.4 mmol), and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 13.5 g of Compound 2-63. (Yield: 70%, MS: [M+H].sup.+=704)

Synthesis Example 2-64

[0389] ##STR00526##

[0390] Compound sub52 (10 g, 107.4 mmol), Compound sub2-C-1 (82.3 g, 225.5 mmol), and sodium tert-butoxide (25.8 g, 268.4 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (1.1 g, 2.1 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 41 g of Compound 2-64. (Yield: 51%, MS: [M+H].sup.+=750)

Synthesis Example 2-65

[0391] ##STR00527##

[0392] Compound sub46 (10 g, 59.1 mmol), Compound sub2-C-1 (45.3 g, 124.1 mmol), and sodium tert-butoxide (14.2 g, 147.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 31.2 g of Compound 2-65. (Yield: 64%, MS: [M+H].sup.+=826)

Synthesis Example 2-66

[0393] ##STR00528##

[0394] Compound sub60 (10 g, 45.6 mmol), Compound sub2-C-1 (34.9 g, 95.8 mmol), and sodium tert-butoxide (11 g, 114 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 26.7 g of Compound 2-66. (Yield: 67%, MS: [M+H].sup.+=876)

Synthesis Example 2-67

[0395] ##STR00529##

[0396] Compound sub61 (10 g, 54.6 mmol), Compound sub2-C-1 (41.8 g, 114.6 mmol), and sodium tert-butoxide (13.1 g, 136.5 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.1 mmol) was added thereto. When the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 32.1 g of Compound 2-67. (Yield: 70%, MS: [M+H].sup.+=840)

Synthesis Example 2-68

[0397] ##STR00530##

[0398] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-62 (15.6 g, 38.1 mmol), and sodium tert-butoxide (4.3 g, 45.01 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.6 g of Compound 2-68. (Yield: 55%, MS: [M+H].sup.+=663)

Synthesis Example 2-69

[0399] ##STR00531##

[0400] Compound sub2-A-1 (10 g, 34.6 mmol), Compound sub2-63 (16.2 g, 38.1 mmol), and sodium tert-butoxide (4.8 g, 19.5 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. When the reaction was completed after 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 12.6 g of Compound 2-69. (Yield: 54%, MS: [M+H].sup.+=677)

Synthesis Example 2-70

[0401] ##STR00532## ##STR00533##

[0402] Compound sub2-C-1 (10 g, 27.4 mmol), Compound sub2-64 (7.8 g, 30.1 mmol), and sodium tert-butoxide (3.8 g, 39.2 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. When the reaction was completed after 2 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 11.2 g of Compound sub2-B-10. (Yield: 70%, MS: [M+H].sup.+=587)

[0403] Compound sub2-B-10 (10 g, 17 mmol), Compound sub2-A-1 (5.4 g, 18.7 mmol), and sodium tert-butoxide (2.4 g, 24.4 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. When the reaction was completed after 3 hours, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was again completely dissolved in chloroform, washed twice with water, and then the organic layer was separated, treated with anhydrous magnesium sulfate and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column chromatography to prepare 8.7 g of Compound 2-70. (Yield: 61%, MS: [M+H].sup.+=839)

Example 1

[0404] A glass substrate on which a thin film of ITO (indium tin oxide) was coated in a thickness of 1000 was put into distilled water containing a detergent dissolved therein and ultrasonically washed. In this case, the detergent used was a product commercially available from Fischer Co. and the distilled water was one which had been twice filtered by using a filter commercially available from Millipore Co. The ITO was cleaned for 30 minutes, and ultrasonic cleaning was then repeated twice for 10 minutes by using distilled water. After the cleaning with distilled water was completed, the substrate was ultrasonically washed with the solvents of isopropyl alcohol, acetone, and methanol, and dried, after which it was transported to a plasma cleaner. Then, the substrate was cleaned with oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.

[0405] On the ITO transparent electrode thus prepared, the following compound HI-1 was formed to a thickness of 1150 as a hole injection layer, but the following compound A-1 was p-doped at a concentration of 1.5 wt. %. The following compound HT-1 was vacuum deposited on the hole injection layer to form a hole transport layer with a layer thickness of 800 . Then, the following compound EB-1 was vacuum deposited on the hole transport layer to a layer thickness of 150 to form an electron blocking layer. Then, Compound 1-1 and Compound 2-1 as the host and the following Compound Dp-7 as the dopant were vacuum deposited in a weight ratio of 49:49:2 on the EB-1 deposited layer to form a red light emitting layer with a layer thickness of 400 . The following compound HB-1 was vacuum deposited on the light emitting layer to a layer thickness of 30 to form a hole blocking layer. The following compound ET-1 and the following compound LiQ were vacuum deposited in a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a layer thickness of 300 . Lithium fluoride (LiF) and aluminum were sequentially deposited to have a thickness of 12 and 1,000 , respectively, on the electron injection and transport layer, thereby forming a cathode.

##STR00534## ##STR00535##

[0406] In the above-mentioned processes, the deposition rates of the organic materials were maintained at 0.40.7 /sec, the deposition rates of lithium fluoride and aluminum of the cathode were maintained at 0.3 /sec and 2 /sec, respectively, and the degree of vacuum during the deposition was maintained at 210.sup.7510.sup.6 torr, thereby manufacturing an organic light emitting device.

Examples 2 to 220

[0407] The organic light emitting devices were manufactured in the same manner as in Example 1, except that in the organic light emitting device of Example 1, the first host and the second host described in Tables 1 to 5 below were used instead of Compound 1-1 and Compound 2-1.

Comparative Examples 1 to 60

[0408] The organic light emitting devices were manufactured in the same manner as in Example 1, except that in the organic light emitting device of Example 1, the first host described in Tables 6 and 7 below were used instead of Compound 1-1. The structures of Compounds B-1 to B-12 of Tables 6 and 7 are as follows.

##STR00536## ##STR00537## ##STR00538## ##STR00539##

Comparative Examples 61 to 156

[0409] The organic light emitting devices were manufactured in the same manner as in Example 1, except that in the organic light emitting device of Example 1, the second host described in Tables 8 to 10 below were used instead of Compound 2-1. The structures of Compounds C-1 to C-12 of Tables 8 to 10 are as follows.

##STR00540## ##STR00541## ##STR00542## ##STR00543##

Experimental Example

[0410] The voltage and efficiency were measured (based on 15 mA/cm.sup.2) by applying a current to the organic light emitting devices manufactured in Examples 1 to 220 and Comparative Examples 1 to 156, and the results are shown in Tables 1 to 4 below. Lifetime T95 means the time required for the luminance to be reduced to 95% of the initial luminance (6,000 nit).

TABLE-US-00001 TABLE 1 Effi- First Second Voltage ciency Lifetime Host Host (V) (cd/A) T95(hr) Color Example 1 Compound Compound 3.59 21.67 237 Red 1-1 2-1 Example 2 Compound 3.61 21.20 215 Red 2-27 Example 3 Compound 3.61 21.88 238 Red 2-39 Example 4 Compound 3.54 21.58 238 Red 2-54 Example 5 Compound 3.52 21.43 241 Red 2-60 Example 6 Compound Compound 3.54 21.82 214 Red 1-2 2-3 Example 7 Compound 3.67 21.79 236 Red 2-10 Example 8 Compound 3.55 21.43 220 Red 2-68 Example 9 Compound 3.64 21.48 225 Red 2-44 Example 10 Compound 3.66 21.72 227 Red 2-49 Example 11 Compound Compound 3.53 22.37 258 Red 1-4 2-5 Example 12 Compound 3.49 22.61 252 Red 2-14 Example 13 Compound 3.54 22.17 260 Red 2-23 Example 14 Compound 3.54 22.55 254 Red 2-58 Example 15 Compound 3.48 23.00 259 Red 2-64 Example 16 Compound Compound 3.52 23.07 263 Red 1-5 2-17 Example 17 Compound 3.52 22.22 254 Red 2-20 Example 18 Compound 3.55 22.88 232 Red 2-28 Example 19 Compound 3.52 22.24 246 Red 2-35 Example 20 Compound 3.48 23.20 262 Red 2-57 Example 21 Compound Compound 3.65 21.75 231 Red 1-6 2-1 Example 22 Compound 3.52 21.33 237 Red 2-27 Example 23 Compound 3.65 21.34 224 Red 2-39 Example 24 Compound 3.53 21.74 234 Red 2-54 Example 25 Compound 3.64 21.97 219 Red 2-60 Example 26 Compound Compound 3.65 21.52 231 Red 1-7 2-3 Example 27 Compound 3.58 21.87 247 Red 2-10 Example 28 Compound 3.59 21.35 234 Red 2-68 Example 29 Compound 3.56 22.30 218 Red 2-44 Example 30 Compound 3.59 22.18 244 Red 2-49 Example 31 Compound Compound 3.45 22.18 263 Red 1-9 2-5 Example 32 Compound 3.41 22.23 279 Red 2-14 Example 33 Compound 3.38 22.21 281 Red 2-23 Example 34 Compound 3.37 22.15 260 Red 2-58 Example 35 Compound 3.38 21.77 277 Red 2-64 Example 36 Compound Compound 3.47 22.16 255 Red 1-11 2-17 Example 37 Compound 3.37 21.21 262 Red 2-20 Example 38 Compound 3.37 22.23 259 Red 2-28 Example 39 Compound 3.45 22.27 277 Red 2-35 Example 40 Compound 3.41 21.94 254 Red 2-70 Example 41 Compound Compound 3.44 23.03 252 Red 1-12 2-1 Example 42 Compound 3.50 22.87 257 Red 2-27 Example 43 Compound 3.45 22.80 254 Red 2-39 Example 44 Compound 3.51 22.15 261 Red 2-54 Example 45 Compound 3.53 22.63 248 Red 2-60

TABLE-US-00002 TABLE 2 Effi- First Second Voltage ciency Lifetime Host Host (V) (cd/A) T95(hr) Color Example 46 Compound Compound 3.51 22.65 263 Red 1-14 2-3 Example 47 Compound 3.48 22.55 242 Red 2-10 Example 48 Compound 3.51 22.33 254 Red 2-68 Example 49 Compound 3.54 22.23 232 Red 2-44 Example 50 Compound 3.54 22.13 257 Red 2-49 Example 51 Compound Compound 3.45 21.81 281 Red 1-15 2-5 Example 52 Compound 3.42 22.14 280 Red 2-14 Example 53 Compound 3.42 22.23 267 Red 2-23 Example 54 Compound 3.44 21.45 255 Red 2-58 Example 55 Compound 3.35 21.33 254 Red 2-64 Example 56 Compound Compound 3.62 21.24 208 Red 1-17 2-17 Example 57 Compound 3.65 21.85 228 Red 2-20 Example 58 Compound 3.57 22.09 232 Red 2-28 Example 59 Compound 3.52 21.29 232 Red 2-35 Example 60 Compound 3.65 21.60 206 Red 2-57 Example 61 Compound Compound 3.66 21.41 221 Red 1-18 2-1 Example 62 Compound 3.55 21.38 218 Red 2-27 Example 63 Compound 3.62 21.54 229 Red 2-39 Example 64 Compound 3.55 22.13 219 Red 2-54 Example 65 Compound 3.64 21.34 225 Red 2-60 Example 66 Compound Compound 3.88 19.7 227 Red 1-19 2-3 Example 67 Compound 3.84 20.8 218 Red 2-10 Example 68 Compound 3.78 19.3 215 Red 2-68 Example 69 Compound 3.82 19.5 220 Red 2-44 Example 70 Compound 3.86 20.2 218 Red 2-49 Example 71 Compound Compound 3.98 20.3 256 Red 1-23 2-5 Example 72 Compound 3.92 20.0 248 Red 2-14 Example 73 Compound 3.95 20.5 251 Red 2-23 Example 74 Compound 3.90 20.1 252 Red 2-58 Example 75 Compound 3.93 19.8 265 Red 2-64 Example 76 Compound Compound 3.60 21.33 223 Red 1-24 2-1 Example 77 Compound 3.58 21.44 223 Red 2-27 Example 78 Compound 3.61 22.16 209 Red 2-39 Example 79 Compound 3.56 21.83 224 Red 2-54 Example 80 Compound 3.59 21.35 234 Red 2-60 Example 81 Compound Compound 3.61 21.90 215 Red 1-25 2-17 Example 82 Compound 3.54 22.23 218 Red 2-20 Example 83 Compound 3.52 21.61 217 Red 2-28 Example 84 Compound 3.63 21.55 209 Red 2-35 Example 85 Compound 3.64 21.29 220 Red 2-70 Example 86 Compound Compound 3.67 21.52 223 Red 1-26 2-3 Example 87 Compound 3.62 21.60 223 Red 2-10 Example 88 Compound 3.60 21.29 209 Red 2-68 Example 89 Compound 3.63 21.39 224 Red 2-44 Example 90 Compound 3.73 20.87 234 Red 2-49

TABLE-US-00003 TABLE 3 Effi- First Second Voltage ciency Lifetime Host Host (V) (cd/A) T95(hr) Color Example 91 Compound Compound 3.66 20.84 215 Red 1-27 2-5 Example 92 Compound 3.66 21.49 218 Red 2-14 Example 93 Compound 3.61 21.46 217 Red 2-23 Example 94 Compound 3.60 21.34 209 Red 2-58 Example 95 Compound 3.66 21.43 220 Red 2-64 Example 96 Compound Compound 3.59 21.76 211 Red 1-29 2-17 Example 97 Compound 3.61 21.73 231 Red 2-20 Example 98 Compound 3.65 21.85 231 Red 2-28 Example 99 Compound 3.64 21.41 214 Red 2-35 Example 100 Compound 3.64 21.78 214 Red 2-57 Example 101 Compound Compound 3.71 21.17 209 Red 1-31 2-1 Example 102 Compound 3.69 21.55 233 Red 2-27 Example 103 Compound 3.70 21.38 205 Red 2-39 Example 104 Compound 3.66 21.18 225 Red 2-54 Example 105 Compound 3.72 21.39 219 Red 2-60 Example 106 Compound Compound 3.73 21.44 217 Red 1-32 2-3 Example 107 Compound 3.70 21.64 206 Red 2-10 Example 108 Compound 3.64 21.52 214 Red 2-68 Example 109 Compound 3.68 21.52 215 Red 2-44 Example 110 Compound 3.64 21.44 234 Red 2-49 Example 111 Compound Compound 3.57 21.53 219 Red 1-33 2-5 Example 112 Compound 3.64 21.38 218 Red 2-14 Example 113 Compound 3.67 21.71 223 Red 2-23 Example 114 Compound 3.63 22.16 220 Red 2-58 Example 115 Compound 3.54 21.21 218 Red 2-64 Example 116 Compound Compound 3.36 22.28 290 Red 1-34 2-17 Example 117 Compound 3.37 21.77 274 Red 2-20 Example 118 Compound 3.35 21.83 277 Red 2-28 Example 119 Compound 3.41 21.89 265 Red 2-35 Example 120 Compound 3.46 21.86 269 Red 2-70 Example 121 Compound Compound 3.40 22.27 292 Red 1-35 2-1 Example 122 Compound 3.35 21.91 260 Red 2-27 Example 123 Compound 3.42 22.17 288 Red 2-39 Example 124 Compound 3.39 22.07 277 Red 2-54 Example 125 Compound 3.35 21.33 281 Red 2-60 Example 126 Compound Compound 3.54 22.56 256 Red 1-36 2-3 Example 127 Compound 3.45 22.83 247 Red 2-10 Example 128 Compound 3.55 23.12 237 Red 2-68 Example 129 Compound 3.53 22.51 237 Red 2-44 Example 130 Compound 3.46 22.30 239 Red 2-49 Example 131 Compound Compound 3.49 23.08 255 Red 1-38 2-5 Example 132 Compound 3.45 23.11 252 Red 2-14 Example 133 Compound 3.56 22.43 233 Red 2-23 Example 134 Compound 3.45 22.65 267 Red 2-58 Example 135 Compound 3.50 22.70 256 Red 2-64

TABLE-US-00004 TABLE 4 Effi- First Second Voltage ciency Lifetime Host Host (V) (cd/A) T95(hr) Color Example 136 Compound Compound 3.42 22.29 284 Red 1-39 2-17 Example 137 Compound 3.40 21.58 258 Red 2-20 Example 138 Compound 3.46 21.57 291 Red 2-28 Example 139 Compound 3.40 21.48 262 Red 2-35 Example 140 Compound 3.44 21.43 267 Red 2-57 Example 141 Compound Compound 3.45 22.23 281 Red 1-40 2-1 Example 142 Compound 3.38 21.54 271 Red 2-27 Example 143 Compound 3.40 21.56 267 Red 2-39 Example 144 Compound 3.35 21.91 265 Red 2-54 Example 145 Compound 3.40 21.33 265 Red 2-60 Example 146 Compound Compound 3.45 23.16 274 Red 1-42 2-3 Example 147 Compound 3.36 23.98 285 Red 2-10 Example 148 Compound 3.47 23.81 274 Red 2-68 Example 149 Compound 3.41 24.14 266 Red 2-44 Example 150 Compound 3.43 23.04 265 Red 2-49 Example 151 Compound Compound 3.37 23.52 275 Red 1-43 2-5 Example 152 Compound 3.44 23.20 273 Red 2-14 Example 153 Compound 3.42 23.57 274 Red 2-23 Example 154 Compound 3.35 23.84 256 Red 2-58 Example 155 Compound 3.44 23.09 264 Red 2-64 Example 156 Compound Compound 3.72 21.0 275 Red 1-44 2-1 Example 157 Compound 3.70 22.1 271 Red 2-27 Example 158 Compound 3.75 21.5 284 Red 2-39 Example 159 Compound 3.74 21.3 268 Red 2-54 Example 160 Compound 3.71 22.3 275 Red 2-60 Example 161 Compound Compound 3.45 21.65 280 Red 1-47 2-3 Example 162 Compound 3.37 21.49 261 Red 2-10 Example 163 Compound 3.44 21.78 257 Red 2-68 Example 164 Compound 3.41 21.25 262 Red 2-44 Example 165 Compound 3.47 21.48 283 Red 2-49 Example 166 Compound Compound 3.38 21.77 290 Red 1-48 2-5 Example 167 Compound 3.42 21.61 274 Red 2-14 Example 168 Compound 3.43 21.59 259 Red 2-23 Example 169 Compound 3.42 22.16 290 Red 2-58 Example 170 Compound 3.43 21.47 287 Red 2-64 Example 171 Compound Compound 3.37 23.86 273 Red 1-49 2-17 Example 172 Compound 3.42 23.92 284 Red 2-20 Example 173 Compound 3.44 23.41 279 Red 2-28 Example 174 Compound 3.38 23.45 258 Red 2-35 Example 175 Compound 3.40 24.15 273 Red 2-57 Example 176 Compound Compound 3.37 23.63 255 Red 1-50 2-1 Example 177 Compound 3.43 24.11 262 Red 2-27 Example 178 Compound 3.41 23.51 282 Red 2-39 Example 179 Compound 3.38 23.92 276 Red 2-54 Example 180 Compound 3.38 24.07 255 Red 2-60

TABLE-US-00005 TABLE 5 Effi- First Second Voltage ciency Lifetime Host Host (V) (cd/A) T95(hr) Color Example 181 Compound Compound 3.37 23.84 287 Red 1-51 2-3 Example 182 Compound 3.35 23.27 272 Red 2-10 Example 183 Compound 3.45 23.37 292 Red 2-68 Example 184 Compound 3.47 23.41 262 Red 2-44 Example 185 Compound 3.46 23.25 271 Red 2-49 Example 186 Compound Compound 3.65 21.36 220 Red 1-52 2-5 Example 187 Compound 3.61 21.58 206 Red 2-14 Example 188 Compound 3.61 21.78 224 Red 2-23 Example 189 Compound 3.60 22.24 208 Red 2-58 Example 190 Compound 3.66 21.30 223 Red 2-64 Example 191 Compound Compound 3.63 21.90 209 Red 1-54 2-17 Example 192 Compound 3.65 21.38 220 Red 2-20 Example 193 Compound 3.59 21.76 205 Red 2-28 Example 194 Compound 3.55 21.57 233 Red 2-35 Example 195 Compound 3.53 21.57 230 Red 2-70 Example 196 Compound Compound 3.57 22.19 245 Red 1-55 2-1 Example 197 Compound 3.56 22.09 226 Red 2-27 Example 198 Compound 3.60 21.40 220 Red 2-39 Example 199 Compound 3.58 21.28 225 Red 2-54 Example 200 Compound 3.65 21.53 225 Red 2-60 Example 201 Compound Compound 3.66 21.30 228 Red 1-54 2-3 Example 202 Compound 3.60 21.53 220 Red 2-10 Example 203 Compound 3.56 22.17 242 Red 2-68 Example 204 Compound 3.52 22.12 241 Red 2-44 Example 205 Compound 3.58 21.87 227 Red 2-49 Example 206 Compound Compound 3.65 21.22 215 Red 1-56 2-5 Example 207 Compound 3.58 22.20 233 Red 2-14 Example 208 Compound 3.53 21.24 210 Red 2-23 Example 209 Compound 3.64 21.30 210 Red 2-58 Example 210 Compound 3.52 21.57 225 Red 2-64 Example 211 Compound Compound 3.56 21.51 208 Red 1-57 2-17 Example 212 Compound 3.54 21.57 226 Red 2-20 Example 213 Compound 3.63 21.57 205 Red 2-28 Example 214 Compound 3.61 22.30 214 Red 2-35 Example 215 Compound 3.61 21.71 217 Red 2-70 Example 216 Compound Compound 3.52 21.27 220 Red 1-59 2-1 Example 217 Compound 3.56 21.89 243 Red 2-27 Example 218 Compound 3.58 22.03 216 Red 2-39 Example 219 Compound 3.64 22.02 219 Red 2-54 Example 220 Compound 3.55 22.00 235 Red 2-60

TABLE-US-00006 TABLE 6 Effi- First Second Voltage ciency Lifetime Host Host (V) (cd/A) T95(hr) Color Comparative Compound Compound 4.10 17.64 123 Red Example 1 B-1 2-1 Comparative Compound 4.12 18.54 105 Red Example 2 2-27 Comparative Compound 4.12 18.57 113 Red Example 3 2-39 Comparative Compound 4.02 18.23 126 Red Example 4 2-54 Comparative Compound 4.01 17.39 112 Red Example 5 2-60 Comparative Compound Compound 4.05 17.36 113 Red Example 6 B-2 2-3 Comparative Compound 4.01 17.53 115 Red Example 7 2-10 Comparative Compound 4.10 18.37 121 Red Example 8 2-68 Comparative Compound 4.13 18.04 122 Red Example 9 2-44 Comparative Compound 4.10 17.25 125 Red Example 10 2-49 Comparative Compound Compound 4.09 17.74 122 Red Example 11 B-3 2-5 Comparative Compound 4.10 18.00 118 Red Example 12 2-14 Comparative Compound 4.10 18.50 106 Red Example 13 2-23 Comparative Compound 4.07 18.30 113 Red Example 14 2-58 Comparative Compound 4.05 17.39 121 Red Example 15 2-64 Comparative Compound Compound 4.01 17.98 111 Red Example 16 B-4 2-17 Comparative Compound 4.08 17.96 124 Red Example 17 2-20 Comparative Compound 4.09 17.44 120 Red Example 18 2-28 Comparative Compound 4.02 18.10 109 Red Example 19 2-35 Comparative Compound 4.12 18.04 108 Red Example 20 2-57 Comparative Compound Compound 4.10 16.81 95 Red Example 21 B-5 2-1 Comparative Compound 4.12 17.15 103 Red Example 22 2-27 Comparative Compound 4.14 16.81 93 Red Example 23 2-39 Comparative Compound 4.11 16.99 93 Red Example 24 2-54 Comparative Compound 4.16 17.13 103 Red Example 25 2-60 Comparative Compound Compound 4.16 16.98 96 Red Example 26 B-6 2-3 Comparative Compound 4.26 17.13 105 Red Example 27 2-10 Comparative Compound 4.13 17.29 101 Red Example 28 2-68 Comparative Compound 4.13 17.15 105 Red Example 29 2-44 Comparative Compound 4.14 16.84 106 Red Example 30 2-49

TABLE-US-00007 TABLE 7 Effi- First Second Voltage ciency Lifetime Host Host (V) (cd/A) T95(hr) Color Comparative Compound Compound 4.11 18.12 142 Red Example 31 B-7 2-5 Comparative Compound 4.05 17.77 139 Red Example 32 2-14 Comparative Compound 4.08 17.90 138 Red Example 33 2-23 Comparative Compound 4.09 17.30 152 Red Example 34 2-58 Comparative Compound 4.03 17.99 136 Red Example 35 2-64 Comparative Compound Compound 4.12 18.35 135 Red Example 36 B-8 2-17 Comparative Compound 4.07 18.30 155 Red Example 37 2-20 Comparative Compound 4.08 18.13 153 Red Example 38 2-28 Comparative Compound 4.07 18.58 145 Red Example 39 2-35 Comparative Compound 4.13 17.84 146 Red Example 40 2-57 Comparative Compound Compound 4.09 18.14 151 Red Example 41 B-9 2-1 Comparative Compound 4.08 18.00 146 Red Example 42 2-27 Comparative Compound 4.05 17.48 141 Red Example 43 2-39 Comparative Compound 4.08 18.56 142 Red Example 44 2-54 Comparative Compound 4.01 17.49 158 Red Example 45 2-60 Comparative Compound Compound 4.12 18.59 148 Red Example 46 B-10 2-3 Comparative Compound 4.11 18.36 143 Red Example 47 2-10 Comparative Compound 4.05 18.21 140 Red Example 48 2-68 Comparative Compound 4.12 18.01 144 Red Example 49 2-44 Comparative Compound 4.02 18.33 138 Red Example 50 2-49 Comparative Compound Compound 4.04 18.25 122 Red Example 51 B-11 2-5 Comparative Compound 4.09 17.49 115 Red Example 52 2-14 Comparative Compound 4.08 17.88 112 Red Example 53 2-23 Comparative Compound 4.10 17.55 117 Red Example 54 2-58 Comparative Compound 4.04 18.53 116 Red Example 55 2-64 Comparative Compound Compound 4.12 18.32 129 Red Example 56 B-12 2-17 Comparative Compound 4.07 18.46 121 Red Example 57 2-20 Comparative Compound 4.05 18.23 109 Red Example 58 2-28 Comparative Compound 4.06 17.36 105 Red Example 59 2-35 Comparative Compound 4.08 17.39 129 Red Example 60 2-70

TABLE-US-00008 TABLE 8 Effi- First Second Voltage ciency Lifetime Host Host (V) (cd/A) T95(hr) Color Comparative Compound 1- Com- 4.12 19.05 138 Red Example 61 2 pound Comparative Compound 1- C-1 4.02 18.86 141 Red Example 62 11 Comparative Compound 1- 4.09 18.81 136 Red Example 63 15 Comparative Compound 1- 4.10 18.53 142 Red Example 64 28 Comparative Compound 1- 4.11 18.89 138 Red Example 65 33 Comparative Compound 1- 4.01 18.87 135 Red Example 66 40 Comparative Compound 1- 4.12 18.66 136 Red Example 67 43 Comparative Compound 1- 4.10 19.14 139 Red Example 68 55 Comparative Compound 1- Com- 4.11 18.40 152 Red Example 69 3 pound Comparative Compound 1- C-2 4.08 19.28 139 Red Example 70 7 Comparative Compound 1- 4.07 15.3 109 Red Example 71 17 Comparative Compound 1- 4.01 14.9 102 Red Example 72 24 Comparative Compound 1- 4.06 15.7 123 Red Example 73 37 Comparative Compound 1- 4.03 16.0 127 Red Example 74 47 Comparative Compound 1- 4.11 15.4 120 Red Example 75 48 Comparative Compound 1- 4.03 15.1 114 Red Example 76 58 Comparative Compound 1- Com- 4.11 18.03 158 Red Example 77 9 pound Comparative Compound 1- C-3 4.05 17.66 150 Red Example 78 16 Comparative Compound 1- 4.04 18.22 144 Red Example 79 22 Comparative Compound 1- 4.13 17.78 134 Red Example 80 38 Comparative Compound 1- 4.07 17.47 134 Red Example 81 41 Comparative Compound 1- 4.04 17.27 148 Red Example 82 45 Comparative Compound 1- 4.05 17.64 151 Red Example 83 53 Comparative Compound 1- 4.04 18.51 135 Red Example 84 57 Comparative Compound 1- Com- 4.12 18.33 137 Red Example 85 2 pound Comparative Compound 1- C-4 4.05 17.62 134 Red Example 86 14 Comparative Compound 1- 4.03 17.31 144 Red Example 87 20 Comparative Compound 1- 4.03 17.80 137 Red Example 88 27 Comparative Compound 1- 4.07 17.59 152 Red Example 89 31 Comparative Compound 1- 4.02 18.31 151 Red Example 90 44 Comparative Compound 1- 4.10 17.87 146 Red Example 91 51 Comparative Compound 1- 4.06 17.96 138 Red Example 92 59 Comparative Compound 1- Com- 4.22 17.11 97 Red Example 93 2 pound Comparative Compound 1- C-5 4.21 17.38 100 Red Example 94 11 Comparative Compound 1- 4.19 17.20 100 Red Example 95 15 Comparative Compound 1- 4.09 16.85 102 Red Example 96 28 Comparative Compound 1- 4.19 16.90 106 Red Example 97 33 Comparative Compound 1- 4.18 17.29 101 Red Example 98 40 Comparative Compound 1- 4.22 17.37 100 Red Example 99 43 Comparative Compound 1- 4.21 17.18 98 Red Example 100 55

TABLE-US-00009 TABLE 9 Effi- First Second Voltage ciency Lifetime Host Host (V) (cd/A) T95(hr) Color Comparative Compound 1- Com- 4.11 17.36 104 Red Example 101 3 pound Comparative Compound 1- C-6 4.14 17.22 94 Red Example 102 7 Comparative Compound 1- 4.18 17.31 95 Red Example 103 17 Comparative Compound 1- 4.13 17.38 98 Red Example 104 24 Comparative Compound 1- 4.17 17.33 102 Red Example 105 37 Comparative Compound 1- 4.16 17.40 101 Red Example 106 47 Comparative Compound 1- 4.17 16.99 99 Red Example 107 48 Comparative Compound 1- 4.13 17.28 96 Red Example 108 58 Comparative Compound 1- Com- 4.01 17.64 139 Red Example 109 9 pound Comparative Compound 1- C-7 4.09 18.24 155 Red Example 100 16 Comparative Compound 1- 4.02 17.79 147 Red Example 111 22 Comparative Compound 1- 4.08 17.20 138 Red Example 112 38 Comparative Compound 1- 4.03 18.57 146 Red Example 113 41 Comparative Compound 1- 4.04 17.67 154 Red Example 114 45 Comparative Compound 1- 4.06 17.24 153 Red Example 115 53 Comparative Compound 1- 4.07 17.51 135 Red Example 116 57 Comparative Compound 1- Com- 4.06 17.74 111 Red Example 117 2 pound Comparative Compound 1- C-8 4.02 17.42 125 Red Example 118 14 Comparative Compound 1- 4.07 17.90 127 Red Example 119 20 Comparative Compound 1- 4.11 18.18 112 Red Example 120 27 Comparative Compound 1- 4.09 17.63 103 Red Example 121 31 Comparative Compound 1- 4.12 18.57 120 Red Example 122 44 Comparative Compound 1- 4.12 18.27 107 Red Example 123 51 Comparative Compound 1- 4.04 17.41 124 Red Example 124 59 Comparative Compound 1- Com- 4.05 19.19 148 Red Example 125 2 pound Comparative Compound 1- C-9 4.11 19.06 159 Red Example 126 11 Comparative Compound 1- 4.13 18.57 155 Red Example 127 15 Comparative Compound 1- 4.05 18.65 158 Red Example 128 28 Comparative Compound 1- 4.07 18.79 160 Red Example 129 33 Comparative Compound 1- 4.01 19.23 150 Red Example 130 40 Comparative Compound 1- 4.09 18.94 151 Red Example 131 43 Comparative Compound 1- 4.01 19.13 146 Red Example 132 55 Comparative Compound 1- Com- 4.03 18.22 108 Red Example 133 3 pound Comparative Compound 1- C-10 4.10 18.33 109 Red Example 134 7 Comparative Compound 1- 4.03 18.08 113 Red Example 135 17 Comparative Compound 1- 4.13 18.37 119 Red Example 136 24 Comparative Compound 1- 4.06 18.38 114 Red Example 137 37 Comparative Compound 1- 4.05 18.09 113 Red Example 138 47 Comparative Compound 1- 4.02 18.05 113 Red Example 139 48 Comparative Compound 1- 4.02 17.49 118 Red Example 140 58

TABLE-US-00010 TABLE 10 Effi- First Second Voltage ciency Lifetime Host Host (V) (cd/A) T95(hr) Color Comparative Compound 1- Com- 4.09 18.04 109 Red Example 141 9 pound Comparative Compound 1- C-11 4.09 17.78 103 Red Example 142 16 Comparative Compound 1- 4.09 18.27 106 Red Example 143 22 Comparative Compound 1- 4.01 18.43 107 Red Example 144 38 Comparative Compound 1- 4.10 17.89 120 Red Example 145 41 Comparative Compound 1- 4.06 17.82 116 Red Example 146 45 Comparative Compound 1- 4.09 18.53 131 Red Example 147 53 Comparative Compound 1- 4.07 17.33 119 Red Example 148 57 Comparative Compound 1- Com- 4.03 17.21 150 Red Example 149 2 pound Comparative Compound 1- C-12 4.02 17.52 153 Red Example 150 14 Comparative Compound 1- 4.07 18.30 154 Red Example 151 20 Comparative Compound 1- 4.10 17.41 135 Red Example 152 27 Comparative Compound 1- 4.10 17.54 152 Red Example 153 31 Comparative Compound 1- 4.01 17.52 160 Red Example 154 44 Comparative Compound 1- 4.05 17.77 151 Red Example 155 51 Comparative Compound 1- 4.04 18.59 155 Red Example 156 59

[0411] When a current was applied to the organic light emitting devices manufactured in Examples 1 to 220 and Comparative Examples 1 to 156, the results shown in Tables 1 to 10 were obtained. In the red organic light emitting device of Comparative Example 1, conventionally widely used materials were used, and Compound EB-1 was used as the electron blocking layer, and Dp-7 was used as the dopant for the red light emitting layer. When Comparative Examples Compounds B-1 to B-12 and the compound of Chemical Formula 2 of the present disclosure were co-deposited and used as a red light emitting layer as shown in Table 6 and Table 7, the driving voltage generally increased and the efficiency and lifetime decreased as compared with the combination of the present disclosure. Even when Comparative Example Compounds C-1 to C-12 and the compounds of Chemical Formula 1 of the present disclosure were co-deposited and used as a red light emitting layer as shown in Tables 8 to 10 above, the driving voltage increased, and the efficiency and lifetime decreased.

[0412] From the above results, it could be confirmed that when a combination of the compound of Chemical Formula 1, which is a first host, and the compound of Chemical Formula 2, which is a second host of the present disclosure, is used in an organic light emitting device, it is advantageous for energy transfer to the red dopant in the red light emitting layer, thus improving the driving voltage and increasing the efficiency and lifetime. Ultimately, this is considered to be because as compared with the combination with Comparative Example Compound, the combination of the compound of Chemical Formula 1 and the compound of Chemical Formula 2 of the present disclosure allows electrons and holes to combine to form excitons through a more stable balance within the light emitting layer, thus increasing efficiency and lifetime. In conclusion, it was confirmed that when the compound of Chemical Formula 1 and the compound of Chemical Formula 2 were combined and co-evaporated and used as a host for the red light emitting layer, the driving voltage, luminous efficiency and lifetime characteristics of the organic light emitting devices can be improved

TABLE-US-00011 Description of Symbols 1: substrate 2: anode 3: light emitting layer 4: cathode 5: hole injection layer 6: hole transport layer 7: electron blocking layer 8: hole blocking layer 9: electron injection and transport layer