TW201245173A - Method for making a condensed polycyclic compound containing chalcogen - Google Patents

Abstract

This invention provides a method for making a condensed polycyclic compound containing chalcogen, the method comprising the following steps: 1. obtaining an aromatic heterocyclic compound (2a) represented by the following formula (2a) by reacting an aromatic heterocyclic compound represented by the following formula (1a) with N-halocarboxylic acid amide under the presence of water or alcohol, 2. obtaining a compound (4) represented by the following formula (4) by reacting the aromatic heterocyclic compound (2a) with the aromatic compound (3) represented by the following formula (3) and, 3. obtaining a chalcogen-containing condensed polycyclic compound containing (5) represented by the following formula (5) by reacting the compound (4) with an acid, whereby a condensed polycyclic compound containing chalcogen (5) can be manufactured under moderate reaction conditions.

Description

201245173 VI. Description of the Invention: [Technical Field] The present invention relates to a method for producing a condensed polycyclic compound containing an oxygen group element (chaic〇gen). [Prior Art] As an organic semiconductor material useful in the field of organic electrons such as an organic thin film transistor, US2007/117973 proposes a condensed polycyclic compound containing an oxygen group element, and a condensed polycyclic ring containing a disulfide bond is described herein. The compound of the formula is heated to about 2 Torr in the presence of a transition metal catalyst. However, from an industrial viewpoint, a method of producing a condensed polycyclic compound containing an oxygen group element under milder reaction conditions has been sought. SUMMARY OF THE INVENTION The present invention provides a method for producing a condensed polycyclic compound containing an oxygen group element under mild reaction conditions. That is, the present invention provides a method for producing a condensed polycyclic compound containing an oxygen group element, comprising: Will formula (la) R1 R1

The aromatic heterocyclic compound [aromatic heterocyclic compound (la)] represented by Zi, Z1 ^ (洵) is reacted with halogen carboxamide in the presence of water or an alcohol to obtain the formula (2a) 201245173

The step of the aromatic heterocyclic compound [aromatic heterocyclic compound (2a)] shown; the aromatic heterocyclic compound (2a) and the formula (3)

The aromatic compound [aromatic compound (3)] shown is reacted to obtain the formula (4)

a step of the compound [compound (4)] shown; and reacting the compound (4) with an acid to obtain the formula (5)

The step of the condensed polycyclic compound of the oxygen-containing group element [condensed polycyclic compound (5) containing an oxygen group element] is shown. Here, in the formula, R1 represents an alkyl group having 1 to 20 carbon atoms, Z1 independently represents a sulfur atom or a halogen atom, and Z2 represents an oxygen atom, a sulfur atom or a collision atom. R11, R12, R13 and R14 each independently represent a hydrogen atom, may have a substituent of 324142 7 201245173 an alkyl group having 1 to 30 carbon atoms, an alkyloxy group having 1 to 3 carbon atoms which may have a substituent, may have a substituent An aromatic group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms which may have a substituent, a heteroarylalkyl group having 5 to 30 carbon atoms which may have a substituent, and a carbon number 4 which may have a substituent a heteroaryl group of 30 or a substituted group represented by the formula Si(R) 3 (R 2 independently represents an alkyl group having 1 to 30 carbon atoms which may have a substituent or a carbon number of 6 to 30 which may have a substituent Aromatic base). X1 represents a halogen atom 'X2' represents a leaving group. [Embodiment] Hereinafter, preferred embodiments of the present invention will be described in detail. The aromatic heterocyclic compound (2a) can be obtained by reacting an aromatic heterocyclic compound (la) with a carboxycarboxamide in the presence of water or an alcohol. First, an aromatic heterocyclic compound (1 a) will be described. R of the aromatic heterocyclic compound (la) represents a top group having a carbon number of 1 to 2 Å. Specifically, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, t-butyl, n-pentyl, neopentyl, n-hexyl, 2-ethyl Hexyl, n-heptyl, n-octyl, 2-hexyloctyl, n-decyl, n-decyl, 2-hexyldecyl, n-decyl, n-dodecyl, n-ten Trialkyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl and n-eicosyl . Preferred are methyl, ethyl, n-propyl, =propyl, n-butyl, t-butyl, tert-butyl, n-pentyl, cyclopentadienylhexyl, cyclohexyl, positive _ Heptyl, n-octyl, n-decyl and n-hexa. More preferred are anthracenyl, ethyl, n-propyl, n-butyl, n-pentyl and n-hexyl groups, particularly preferably anthracenyl, ethyl, n-propyl and n-butyl. The aromatic heterocyclic compound (1 phantom 21 independently represents a sulfur atom or selenium 324142 201245173 atom. z1 is preferably a sulfur atom. z2 represents an oxygen atom, a sulfur atom or a collision atom. " Z2 is preferably an oxygen atom or a sulfur atom. More preferably, it is a sulfur atom. In the method of producing an aromatic heterocyclic compound (2a) by reacting an aromatic heterocyclic compound (la) with N-halocarboxyguanamine, the N-halocarboxyguanamine used is 'having

a compound of a partial structure represented by CN-halogen II 0, such as N-haloacetamide such as N-chloroacetamide, N-bromoacetamide or N-iodoacetamide, N-aluminum amber N-halosuccinimide, N-chloroosuccinimide, N-bromo phthalimide, N-bromo, etc., such as Succinimide, N-indicarbamide, N-mothperonimide N-halogen quinone imine, 1,3-dichloro-5,5-dimercapto-indenine 〇^ (1&111:〇111), 酞醯imine, N-mothimine, 1,3-dihaloethylene carbazide such as 1,3-dibromo-5, 5-dimercaptoindolide or 1,3-diiodo-5, 5-dimethylhydantoin. Preferred N-halocarboxyguanamines are N-gas succinimide, N-bromosuccinimide, N-iodosuccinimide, N-chloroimine, N-bromoimine and N-iodoimine, more preferably N-halocarboxyguanamine is N-bromosuccinimide. The amount of N-halocarboxyguanamine used is usually from 0.5 to 15 moles, preferably from 0.7 to 10 moles, per mole of the aromatic heterocyclic compound (la). The ratio is preferably from 1 mole to 8 moles. When the amount of N-halogenated retinoic acid used is too small, the reaction is incomplete, and when the amount used is too large, a side reaction is performed. 324142 9 201245173 N-family secret amine can be used for money, or it can be divided into several times according to the degree of reaction. The reaction of the aromatic heteropoly compound (la) with N-nitramine retinoic acid is carried out in the presence of water or an alcohol. The reaction is usually carried out in a solvent, and water or an alcohol may be added to the solvent before the start of the reaction, and may be added to the amount of the water or the alcohol added in the reaction, and the solvent is usually ι to 1/2 (10) by weight. The ratio is preferably 1/2 to 1/150 weight times, more preferably 1/5 to 1/1 inch weight. Examples of the alcohol include decyl alcohol, ethanol, isopropanol, n-butanol and the like. As a refrigerant, for example, there are aromatic cigarettes such as pentyl alcohol, hexane, and gamma, and aromatic cigarettes, such as A, Ben, and the like, and -, gas, chloroform, 1, 2, and 2 Alkane, 1,2-di-acetone, etc., such as toothed tobacco, diethyl hydrazine, tetranitroanzepine, n 曙 ( (diQxane), cyclofilament methyl methoxide. Moreover, water or alcohol can also be used as a solvent. The amount of the solvent to be used is usually from 1 to 500 times by weight, more preferably from 2 to 300 times by weight, still more preferably from 5 to 200 times by weight, to the aromatic heterocyclic compound (la). The reaction temperature, 诵杳 is usually from -78 ° C to the boiling point of the solvent, preferably from -40 Torr to the boiling point of the solvent, and more preferably "c to the point of the solvent." The reaction time is, for example, in the range of 1 minute to 96 hours. After the completion of the reaction, a general post-treatment is carried out, and if necessary, it can be purified by distillation, recrystallization, and Shih-Hui-gel chromatography to obtain an aromatic heterocyclic compound (5). Specific examples of the aromatic heterocyclic compound (la) include, for example, the following compounds: 324142 10 201245173 R1 R1, Z1 ¥ (1a) Z1 Z2 R1 S 〇ch3 S 〇(ch2) 5ch3 S 〇ch3 SS ch3 SS c2h5 SS (CH2) 3CH3 SS (CH2) 5ch3 SS (ch2) 9ch3 S e S ch3 SS e ch3 SS β (ch2) 5ch3 Specific examples of the aromatic heterocyclic compound (2a) include the following compounds. 324142 11 201245173 •R1 R1, 0=Z1 Z1-0 Z1 Z2 X1 R1 S 〇B r ch3 S 〇Cl ch3 S 〇I (CH2) 5ch3 S e 〇B r ch3 SS Cl ch3 SSB r ch3 SSB r c2h5 SSB r (ch2) 3ch3 SSB r (CH2) 8ch3 SSB r (ch2) 9ch3 S e SB r ch3 SS e B r ch3 SS Θ Cl (ch2) 8ch3 Next, an aromatic heterocyclic compound (2a) and an aromatic compound (3) will be described. The condensation reaction. First, the aromatic compound (3) will be described in detail. R11, R12, R13 and R14 of the compound (3) each independently represent a hydrogen atom, a substituted alkyl group having 1 to 30 carbon atoms, a substituted alkoxy group having 1 to 3 carbon atoms, and may be substituted. An aromatic group having 6 to 30 carbon atoms, an aryl group having 7 to 30 carbon atoms which may be substituted, a heteroarylalkyl group having 5 to 3 carbon atoms which may be substituted, and a carbon number of 4 to 3 G which may be substituted Heteroaryl or formula - 2) 3 疋 324142 201245173 The substituted decyl group (R2 independently represents a substitutable alkyl group having 1 to 30' carbon atoms or a substituted carbon group having 6 to 30 carbon atoms) . The "alkyl group having 1 to 30 carbon atoms which may be substituted with an alkyl group having 1 to 30 carbon atoms" represented by R11, R12, R13 and R14 may be any of a straight chain, a branched chain or a cyclic form. By. Specific examples of the alkyl group having 1 to 30 carbon atoms include, for example, anthracenyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, t-butyl, n-decyl, and new Sulfhydryl, n-hexyl, 2-ethylhexyl, n-heptyl, n-octyl, 2-hexyloctyl, n-decyl, n-decyl, 2-hexyldecyl, n-decene , n-dodecyl, n-tridecyl, n-tetradecyl, n-decyl, n-hexadecane, n-hexadecane, n-octadecyl, Zheng-Nineteen-burning base, positive-twenty-burning base, positive-twenty-one base, positive-twenty-two base, positive-twenty-three base, positive-twenty-four base, positive-twenty a pentane group, a n-bihexyl group, a n-heptyl group, a n-octadecyl group, a n-dodecyl group, a n-tridecyl group, a cyclopentyl group, a cyclohexyl group, and Cycloheptyl or the like, preferably fluorenyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl , 2-ethylhexyl, n-heptyl, n-octyl, n-decyl, n-decyl, 2-hexyldecyl, n-decyl, n-dodecyl, n-ten Three burning , n-tetradecyl, n-decyl, n-hexadecane, n-hexadecane, n-octadecyl, n-nonyl, and t-calcene, More preferred are methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, cyclohexyl, 2-ethylhexyl, n-heptyl, n-octyl, n-decene Base, n-decyl, n-decyl, n-dodecyl, n-tridecyl, 2-hexyloctyl, n-tetradecyl, n-pentadecyl, n- A decyl group having a carbon number of 1 to 16 324142 13 201245173 such as hexadecyl group, cyclohexyl group or cyclopentyl group. The substituent which the "alkyl group having 1 to 30 carbon atoms which may be substituted" has a halogen atom, an alkoxy group having 1 to 30 carbon atoms, or the like. As the halogen atom, for example, a fluorine atom, a gas atom, a bromine atom or the like. As the alkoxy group having 1 to 30 carbon atoms, for example, a methoxy group, an ethoxy group, a n-propoxy group, a n-butoxy group, a n-pentyloxy group, a n-hexyloxy group, a n-heptyloxy group, n-Octyloxy, n-decyloxy, n-decyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-Five-decyloxy, n-hexadecaneoxy, n-hexadecanyloxy, n-octadecyloxy, n-nonoxixyloxy, n-dioxoyloxy, positive- Twenty-one alkoxy, n-docosyloxy, n-docosyloxy, n-tetracosyloxy, n-pentadecyloxy, n-hexadecane alkoxy , • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • The "alkyl group having 1 to 30 carbon atoms which may be substituted" may have a substituent, preferably a fluorine atom. As the fluorine-substituted alkyl group having 1 to 30 carbon atoms, for example, perfluorohexyl, perfluorooctyl, perfluorodecyl, perfluorododecyl and perfluorotridecyl. As the "alkoxy group having 1 to 30 carbon atoms which may be substituted with carbon atoms of 1 to 30" represented by R11, R12, R13 and R14, for example, an anthracene group, an ethoxy group, a positive group - Propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n-decyloxy, n-methoxy, n-alkoxy , n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecanyloxy, n-hexadecaneoxy, n-heptadecanoate, positive - 18 decyloxy, n-.19 alkoxy, n-telephone oxy, n-dioxyl- 324142 14 201245173 oxy, n-twenty oxy, n-twenty-three Alkoxy, n-tetrakisyloxy, n-thopentyloxy, n-hexafluoroalkoxy, n-tapyleneoxy, n-octadecyloxy, positive - a 29-alkoxy group and a n-dodecyloxy group. Preferred are, for example, methoxy, ethoxy, n-propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n- Alkoxy, n-decyloxy, n-oxyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecanyloxy, n-ten Alkoxy groups having 1 to 20 carbon atoms such as alkoxy group, n-heptadecane oxy group, n-octadecyloxy group, n-xanthyloxy group and n-eicosanyl group. The substituent of the "alkoxy group having 1 to 30 carbon atoms which may be substituted", for example, a halogen atom such as an IL atom, a gas atom or a desert atom, an alkoxy group having 1 to 30 carbon atoms, and a carbon number of 6 to 30 An aromatic group, an aralkyl group having 7 to 30 carbon atoms, a heteroaryl group having 4 to 30 carbon atoms, and a heteroarylalkyl group having 5 to 30 carbon atoms. The ruthenium atom contained in the substituent may be substituted by a fluorine atom. As the aromatic group having 6 to 30 carbon atoms, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group or the like can be mentioned. As an aromatic group having 7 to 30 carbon atoms, for example,

The base shown. Here, nl represents an integer from 1 to 14, n2 and ! Ip3 represents an integer from 1 to 10. a heteroaryl group having 4 to 30 carbon atoms means a group substituted with at least one carbon atom of an aromatic ring of an aromatic group, substituted with a hetero atom such as a nitrogen atom, an oxygen atom, a sulfur atom or a collision atom, for example, a β-septylene group,夫,,,,,,,,,,,,,,,,,,, b] thienyl, benzo[b]furanyl and the like. As the heteroaryl group, a thienyl group, a thiazolyl group, a thieno[3,2-b]thienyl group, a benzo[b]thienyl group, a benzo[b]furanyl group is preferable. The heteroaralkyl group having 5 to 30 carbon atoms means a group substituted with at least one carbon atom of an aromatic ring of an aromatic alkyl group, substituted with a hetero atom such as a nitrogen atom, an oxygen atom, a sulfur atom or a selenium atom, and is used as a heteroaromatic group. Base, for example, -(CH2)n4^J| -<CH2W_^一—dj]

-(CH2)n々F _(CF2々 is not a base. Here, n4 represents an integer of 1 to 26, and n5 represents an integer of 1 to 24' n6 represents an integer of 1 to 22. More preferably, it is a formula (-( CH2)n, ^jQ>~(CH2)ne-<^]Q] The base shown here, n4 represents an integer of 1 to 26, n5 represents an integer of 1 to 24, and η6 represents an integer of 1 to 22. The substituent which is "alkoxy group having 1 to 30 carbon atoms which may be substituted" is preferably a fluorine atom. As the substituted alkoxy group having 1 to 30 carbon atoms, for example, perfluorocarbon group, perfluoro group Octyloxy, perfluorodecyloxy, perfluorododecan-1-perfluorotridecyloxy, methoxyethoxyethoxy. The formula "R12, R13 and R14" can be substituted. The "aromatic group" of the carbon number 6 to 324142 201245173 30 is preferably a monocyclic or bicyclic ring, and more preferably, for example, a stupid group, a 1-naphthyl group or a 2-naphthyl group. Substituents of substituted aryl groups having 6 to 30 carbon atoms, such as a gas atom, a chlorine atom, and a functional atom of a odor atom, such as an alkyl group having 1 to 20 carbon atoms and an alkoxy group having 1 to 20 carbon atoms , an aromatic group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, carbon a heteroaryl group of 4 to 20 and a heterocyclic group having 5 to 20 carbon atoms. The hydrogen atom contained in the substituent may be substituted by a hydride atom. As an aromatic group having 6 to 20 carbon atoms, for example, a phenyl group, a naphthyl group, 2_ I group ' as a substituted aryl group having 6 to 20 carbon atoms, for example, may be a wholly-losing group. As a carbon group having 1 to 20 carbon atoms, for example, methyl group, ethyl group, propyl group, n-butyl group, n-pentyl group Base, n-hexyl 'n-heptyl, n-octyl, n-indenyl, n-decyl, n-decyl, n-dome, n-tride, n. Tetraalkyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadesyl, n-octadecyl, n-di | Burning base, positive-twelf burnt base, positive-twenty-three burnt base, positive-twenty-four burn base, positive-twenty-five base, positive-twenty-six base, positive-twenty-seven a group of n-octadecyl, n-yield, and n-decyl. As the R 1 , R 12 , R 13 and R 14 , the substituted aralkyl having 7 to 30 carbon atoms a substituent of a group such as a halogen atom such as a fluorine atom, a chlorine atom or a bromine atom, for example, a carbon number of 1 to 2 Å An alkyl group, an alkoxy group having a carbon number of 2 to 20, an aralkyl group having 7 to 20 carbon atoms, a heteroaryl group having 4 to 20 carbon atoms, and a heteroaryl group having 5 to 20 carbon atoms. The hydrogen atom of the alkyl group, the alkoxy group, the arylalkyl group, the heteroaryl group or the heteroarylalkyl group may be substituted by a fluorine atom. The substituent of the "substituted aralkyl group having 7 to 30 carbon atoms", 324142 17 201245173 is preferably a fluorine atom. As a "substituted aralkyl group having 7 to 30 carbon atoms", for example,

(nl represents an integer of 1 to 24, n2 and n3 represent an integer of 1 to 20), an aralkyl group having 7 to 30 carbon atoms, or a formula

(n4 and n5 represent an integer of 1 to 24, and n6 represents an integer of 1 to 23) an aralkyl group having 7 to 30 carbon atoms which may have a substituent. As the "heteroaromatic group having 4 to 30 carbon atoms which may be substituted" represented by R11, R12, R13 and R14, for example, thienyl, furyl, thiazolyl, thieno[3,2-b]thienyl, furan And [3,2-b]furanyl, thieno[3,2-b]furanyl, benzo[b]thienyl, benzo[b]furanyl. As a preferred heteroaromatic group, for example, a thienyl group, a thiazolyl group, a thieno[3,2-b]nonenyl group, a benzo[b]thienyl group, a benzo[b]furanyl group, particularly represented by the formula The base is ideal. The substituent of the "substitutable heteroaryl group having 4 to 30 carbon atoms which may be substituted", for example, a halogen atom such as a fluorine atom, a gas atom or a bromine atom, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms. An oxy group, an aromatic group having 6 to 20 carbon atoms, 324142 18 201245173 an aryl group having 7 to 20 carbon atoms, a heteroaryl group having 4 to 30 carbon atoms, and a heterocyclic group having 5 to 30 carbon atoms. It is included in the extraction of "when substituted by fluorine atom. As a "substitutable carbon number 4 to 30 heteroaromatic group", for example, 2_ porphinyl, 2, benzo[3, 2__ phenyl, 2 - stupid And [-phenyl, 5-fluoro-2-phenyl, 5-hexyl-2-brenyl, 4-hexyloxy such as exemplyl. a substituent of a "substitutable carbon number of 5 to 30 heteroaryl group" such as a fluorine atom, a gas atom, a bromine atom or the like, an alkyl group having a carbon number of i to 20, and a carbon number of 2 to 2 The alkoxy group, the aralkyl group having 7 to 3 carbon atoms, the heteroaryl group having 4 to 3 carbon atoms, and the heteroaryl group having 5 to 2 carbon atoms. The hydrogen atom contained in the substituent may be substituted with a fluorine atom. The substituent of the "heteroarylalkyl group having 5 to 3 carbon atoms which may be substituted" is preferably a fluorine atom. As the "heteroarylalkyl group having 5 to 3 carbon atoms which may have a substituent", for example, it may be a formula (CH2) n4 to ^j| - • dO - (CH2)^] - (CH2) nS "D -(CH^eOO -{CH2WO〇-(4) - (gas^JF -(CF2)n4^j]) where n4 represents an integer from 1 to 26, n5 represents an integer from 1 to 24, and n6 represents An integer of 丨22. The substitution 324142 201245173 decyl group represented by the formula Si(R2)3 represented by RU, R12, R13 and R14 is preferably a trialkyl group having a fluorine atom and having a carbon number of 3炱30.矽alkyl 'herein' trialkylsulfonyl group means a total of 3 to 30 carbon atoms bonded to three alkyl groups of a ruthenium atom. Therefore, it is recorded in one of the bases of the Shixia atom. A carbon group having a maximum carbon number of 28 and a carbon number of 1 to 3 Å which may be substituted by a fluorine atom. Therefore, as a tricarboyl group which may be substituted by a fluorine atom, it means an alkyl group bonded to a ruthenium atom. a group in which a part or the whole of a hydrogen atom is substituted with a fluorine atom. Specific examples of the trialkylsulfanyl group include, for example, a trimethylsulfonyl group, a triethylsulfanyl group, a tri(isopropyl)decylalkyl group, and a tert-butyl group. Dimethyl decyl, two a hexyl decyl group and a dimethyldodecyl fluorenyl group. X2 of the aromatic compound (3) represents a leaving group. X2 is a condensation reaction between the aromatic compound (3) and the aromatic heterocyclic compound (2a). The leaving group may be, for example, more preferably a group represented by the formula (6) R10. In the formula (6), R1CI independently represents a hydroxyl group, an alkyl group having 1 to 1 carbon number, and an alkoxy group having 1 to 10 carbon atoms. a aryloxy group having 6 to 2 Å of carbon number, r1. The same or different 'may be combined with 2 R1. Together with the butterfly atom, a ring structure is formed, '., as shown by Rie, carbon number 1 to 1 An alkyl group of hydrazine, such as methyl, ethyl n-propyl, isopropyl, n-butyl, t-butyl, t-butyl, n-pentyl, neopentyl, cyclopentyl, n- a linear, branched, or cyclic alkyl group such as a hexyl group, a cyclohexyl group, a n-heptyl group, a n-octyl group, a n-decyl group, a n-decyl group, a fluorene or a 2-dimethyl group. Rl. The carbon number i to the oxime 324142 20 201245173 base 'such as methoxy, ethoxy, n-propoxy, n-butoxy and n-hexyloxy. As shown in ri. Aroma of 6 to 20 carbons a group, for example, a phenoxy group, a fluorenyl group, a naphthyloxy group, and a 2-naphthyloxy group. In combination with two R1 (1, a ring structure is formed together with a boron atom, as a comparative example), for example, 1, 3, 2 - Dioxaborolane, 4'4'5'5, tetradecyl 3,2-dioxaborolan, 5,5-dimethyl-n2-dioxolane, 1,3, a benzod i oxaboro 1 e ring and a 9-cylylene-2,3,1-decane ring. As a specific example of the leaving group, in addition to the group represented by the formula (6), there are also, for example, the formulas (7), (8), and (9) R20 (7) (8) (9) to Sn-R2. , R2〇~~MgX3 —2nX< indicates the departure from the base. In the formula (7), 'R2° independently represents an alkyl group having a carbon number of 1 to 1 Å, a group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, and a second butyl butyl group. Amyl, cyclopentyl, n-hexyl, cyclohexyl, n-octyl. Preferred are methyl, ethyl, n-propyl, n-butyl and more preferably decyl, ethyl, n-propyl and n-butyl. Wherein ' can be different, respectively, but is preferably the same. In the formula (8), the X3矣-上梅工 discusses that the clothes are not atoms, such as fluorine atoms, gas atoms, atoms = atoms. It is preferably a desert atom or a broken atom. In 9), X represents a halogen atom such as a fluorine atom, a gas atom, 324142 21 201245173 atom and a moth atom. Preferred are desert atoms and moth atoms. In the aromatic compound (3), a compound having a group represented by the formula (6) as a leaving group can be produced by a usual method, for example, according to the fourth edition of Experimental Chemistry Lecture 24, Organic Synthesis VI (Sakamoto Chemical Society) ) Method of manufacturing as described on page 80. In the aromatic compound (3), a compound having a group represented by the formula (7) as a leaving group can be produced by a usual method, for example, according to the fourth edition of Experimental Chemistry Lecture 24, Organic Synthesis VI (Edited by Sakamoto Chemical Society). Manufactured by the method described on page 189. In the aromatic compound (3), a compound having a group represented by the formula (8) as a leaving group can be produced by a usual method, for example, according to the fourth edition of Experimental Chemistry Lecture 24, Organic Synthesis VI (Edited by the Chemical Society of Japan) 43 The method described in the page is manufactured. In the aromatic compound (3), a compound having a group represented by the formula (9) as a leaving group can be produced by a usual method, for example, according to the fourth edition of Experimental Chemistry Lecture 24, Organic Synthesis VI (Edited by the Chemical Society of Japan) 401. The method described in the page is manufactured. The aromatic compound (3) may, for example, be a compound represented by the numbers (3-1) to (3-280) in Table 1.

324142 22 201245173 [Table l] No. R1 1 R12 R13 R 1 4 X2 (3-1) Η Η Η Η Β (ΟΗ) 2 (3-2) CH3 Η Η Κΐ Κΐ (3-3) C2Hs Η Η Η Β (OCH3) 2 &lt;3-4) i - C 3Hfl Η Η Η Β (ΟΗ) 2 (3-5) n ~ C 4 H ® Η Η Η Β (ΟΗ) * (3-6) n — C β H j 3 Η Η Η Β (Ο Η) 2 (3-7) Oil·* Η Η Η (3-8) n — C i 2 H 2 e Η Η Η (3-9) ix — C j β H aa Η Η 〈 <3-10) iv — C e F i 3 Η Η Η Β (,ΟΗ) 2 (3-11) OC h3 Η Η Η Sn (η — C4H9) a (3-12) O ( n -C3H7) Η Η Η Β (ΟΗ) 2 (3-13) O (n-CeH13) Η Η Η Β (OH) s (3-14) 〇 ( π - C g F 13) Η Η Η κ] (3-15) - (~ Q ( Η Κ ( ( OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH) a (3-19) ~1~^3~η-°&lt;Ρΐ3 Η Η Η (3-20) Η Η Η Β (ΟΗ) 2 23 324142 201245173 No. Rl 1 R12 R 1 3 R 1 4 X2 (3-21) HHHB (OH) a (3-22) ΚΤ—HHH (3-23) -KTF HHH (3-24) ^Ό〇~〇βΗι7 HHHB (OH) a (3-25) -Saki: HHH (3-26) ^-Q-0CHs HHH (3-27) HHHB (OH) a (3-28) X==/ n-CeFu HHH (3-29) -ι-ζχ0^ HHH Sn (n — C4H9) 3 (3-30) HHHM g B r (3-31) -Si (CH3) a (n -CaHlT) HHHB (OH) 2 (3-32) -|-(CHz)— HHHB (OH) a (3-33) - Bu (CH2)4-^^&quot;&quot;frCeH13 HHHZ η B r (3-34) FFHHHB (OH) a (3-35) HHHB (OH) a 24 324142 201245173

No. Rl 1 Ria R13 R 1 4 X8 (3-36) HHHB (OH) * (3-37) HHHB (OH) 2 (3-38) -S i (CHS) 3 HHH Κΐ (3-39) - S i (C2Hs) 3 HHHB (OH) 2 (3-40) -Si ( i -C a H7) 3 HHHB (OH) 2 (3-41) -Si (C Hs ) , ( t - c 4Hb ) HHH No. R1 1 R12 R13 Rl 4 X2 (3-42) H ch3 HHB (OH) 2 (3-43) H c2h8 HHB (OH) 2 (3-44) H n — C a Η e HHB (OH) 2 ( 3-45) H i-C3He HHB (OH) j (3-46) H n — C 4 H g HHB (OH) 2 (3-47) H s — C 4 H g HHB (OH) 2 (3- 48) H n - C s Η h HHB (OH) 2 (3-49) H ~ HHB (OH) 2 (3-50) H n - C β H i 3 HHB (OH) a (3-51) H • o HHB (OH), (3-52) H CjHb HHB (OH) 2 (3-53) H n - C 7 H , s HHB (OH) 2 (3-54) H 11 — CBH ] 7 HHB ( OH), (3-55) H n — C 9 H j HHB (OH) 2 (3-56) H n—C10H21 HHB (OH) 2 (3-57) H Π-〇βΗι7 n-CeHis HHB (OH ), (3-58) H n — C jj H 2 a HHB (OH) 2 (3-59) H n - C i 2 Η 3 8 HHB (OH) 2 (3-60) H /~n-CaHi3 n-CeHtj HHB (OH) 2 (3-61) H n — C ! a H ar HH • B (OH) 2 25 324142 201245173 No. R1 1 R1 2 R1 3 R1 4 Xa (3-62) Η n — C ι 4 Η a β Η Η Β (Ο Η) 2 (3-63) Η η. — C ι 5 Η a ι Η Η Β (Ο Η ) 2 (3-64) Η η — C t β Η 3 3 Η Η Β (Ο Η) 2 (3-65) Η η — C ι τ Η a 9 Η Η Β (Ο Η) 2 (3-66 Η η _ CJ 0 Η 3 τ Η Η Β (Ο Η) 2 (3-67) Η n— Η Η Β (Ο Η) a (3-68) Η η — CaoHn Η Β Β (ΟΗ) 2 ( 3-69) Η η—Ca8H45 Η Η Β (ΟΗ) 3 (3-70) Η η-C 2„Η5 , Η Η Β (Ο Η) 2 (3-71) Η ιι - C 2 β Η Β 7 Η Β Β (Ο Η) 2 (3-72) Η η — C a 〇Η λ ι Η Η Β (Ο Η) 2 (3-73) Η η - C β F ! a Η Η Β (Ο Η) 2 (3-74) η η - C β F , 7 Η Η Β (ΟΗ) 2 (3-75) Η n — C ▲ 2 F 2 3 Η Η Β (ΟΗ) 2 (3-76) Η OC η3 Η Η Β (Ο Η) 2 (3-77) Η 〇 c2hb Η Β Β (Ο Η) 2 (3-78) Η Ο (η -CsHr) Η Β Β (Ο Η) 8 (3-79) Η Ο( η-C * Hfl) Η Η Β (Ο Η) 2 (3-80) Η Ο ( η - C8 Η ,,) Η Β Β (D Η) 2 (3-81) Η Ο (n-CeHls ) Η Η Β (Ο Η) 2 (3-82) Η Ο ( η - CT Η ,,) Η Η Β (Ο Η) 2 (3-83) Ο ( η - Ce Η t 7 ) Η Η Β (Ο Η) 2 &lt;3-84) Η Ο (n-Cl0Hai) Η Β Β (Ο Η) 2 (3-85) Η Ο (η -C t , Η 2β) Η Η Β (Ο Η) 3 (3-86) Η Ο (η—CieH3g) Η Β Β (Ο Η) 2 (3-87) Η 〇 (π _ C ^ g Η g 7 ) Η Η Β (Ο Η) 3 (3-88) Η Ο (η -CaoH41) Η Η Β (Ο Η) 2 (3-89) Η Ο (π~ Η Β Β (ΟΗ) 2 (3-90) Η 0 (η—C2eH57) Η Η Β (Ο Η) 2 (3-91) Η Ο (n-CaoHei) Η Β Β (ΟΗ) 2 (3-92) Η Ο (n-CeF15) Η Η Β (Ο Η ) Ζ (3-93) Η Ο (n-CeF,,) Η Η Β (Ο Η) 2 (3-94) Η Ο (n—CigF:,) Η Η Β (Ο Η) 2 (3-95 Η -^ο Η Η Β (Ο Η) 2 (3-96) Η Η Η Β (Ο Η) 2 26 324142 201245173 No. Rl 1 Rl a R13 Rl 4 Xa (3-97) Η CHa HH (3- 98) Η CsH5 HH (3-99) Η η — C 3 Η 0 HH (3-100) Η i-CSH0 HHK] (3-101) Η n-C4H9 HH (3-102) Η s-C4He HHS n (CH3) 3 (3-103) Η n - C 5 H » ! HH (3-104) Η n — C 〇H i 3 HH (3-105) Η o HH (3-106) Η ^yn-c4He QzHte HH (3-107) Η n — C a H j 7 HHK House (3-108) Η n — C β H i 〇HHS n (n-3 (3-109) Η n_Cl0Hai HH (3-110) Η n-CeHi7 nC〇Hi3 HH (3-111) Η it a C ii H 2 3 HHM g B r ( 3-112) Η Π—C12H25 HH (3-113) Η &quot;Vn^13 n-Cel-ha HHZ η B r 27 324142 201245173 No. R1 1 R&quot; R1 3 R1 4 Χβ (3-114) Η η — C ! β Η 3 3 Η Κ Κι (3-115) Η η - C ! β Η 3 r Η Η Sn (η—C4Hg) 3 (3-116) Η n ~~ C 2 〇Η 4 ι Η Η ( 3-117) Η η — Ce F &quot; Η Η (3-118) Η η — C 8 F ι τ Η Η Sn (η.—C4H9) 3 (3-119) Η tl— Ci3F 2β Η Η Ζ η Β r (3-120) Η OC η3 Η Η Β (ΟΗ) 2 (3-121) Η ο c2hb Η Κΐ Κΐ (3-122) Η Ο (n-C3H7) Η Η (3-123) Η Ο ( η -C tHg) Η Η (3-124) Η Ο (η -C„H,,) Η Κΐ Κΐ (3-125) Η Ο (n-CeHl3) Η Η 28 324142 201245173 No. R1 1 R12 R1 3 R 1 4 X2 (3-126) Η Η Η Β (ΟΗ) 2 (3-127) Η Η Η Β (OH) a (3-128) Η Η Η Κι (3-129) Η Η Η Β (Ο Η) 2 (3-130) Η 17 Η Η Κΐ (3-131) Η »^10^21 Η Η Μ g Β r (3-132) Η Η Η Sn (η— H 〇Η 〇Η ( ( ( ΟΗ) 2 (3-136) Η |&quot;^^_n-Ce5=i3 Η Η (3-137) Η -丨Λ3 Η Η Β (ΟΗ) 2 29 324142 201245173

Nickname Rl 1 R12 R 1 3 R1 4 X2 (3-138) Η -her0&quot; HHB (OH) 2 (3-139) Η e^rvCeHn Κί HHB (OH) j (3-140) Η HH (3- 141) Η HHB (OH) 2 (3-142) Η -i&lt;JHH Sn (n-C4He) 3 (3-143) Η -i&lt;rn'CeFli HH Κι (3-144) Η -i-&lt; xF HHB (OH) 2 (3-145) Η HHB (OH) a (3-146) Η - shout FHHB (OH) a (3-147) Η -lO&gt;-〇CH, HHK off&lt;3-148 ) Η -i-^-OCaHe HHB (OH) 2 (3-149) Η HHB (OH) 2 (3-150) Η -|-^3_0(,VC5*4,) Η&quot; H Sn (ri-C4He ) 3 (3-151) Η HH &lt;0 (3-152) Η -Ι-^^-ΟΙπ-ΟβΗ,τ) HH 30 324142 201245173 No. Rl 1 R12 R 1 3 Rl 4 X8 (3-153) Η HHB (OH) 2 (3-154) Η HHB (OH) 2 (3-155) Η HH (3-156) Η O(n-CeHia) Otn-Ce^j) HH (3-157) Η HHB ( OH) 2 (3-158) Η -ι&lt;Χ, Ηβ HHB (OH) 2 (3-159) Η -^T〇, nAH, s HH (3-160) Η Heart. · H H S n ( n — C 4 H g ) 9 (3-161) Η heart. , —HHZ η B r (3-162) Η _^^y0, rvC12H2S HHM g B r (3-163) Η HH (3-164) Η 4&lt;T, F17 HHB (OH) 2 (3-165) Η - Strict HHB (OH) 2 (3-166) Η -Si (C H3) 2 (n - C 8 H ! 7 ) HHB (OH), (3-167) Η -Si (C Hs ) a ( n -c10h21) HHB (OH) 2 31 324142 201245173 Compilation R&quot; R12 R13 R1 4 Xa (3-168) Η HHB (OH) a (3-169) Η XHHB (OH) 2 (3-170) Η +(〇Ηί)»~〇HH 咕(3-171) Η -hcH2)10-QHHS n ( n — C * H fl ) 3 (3-172) Η HHM g B r (3-173) Η HHB ( Ο H) 2 (3-174) Η »-CgHl3 HHZ η B r (3-175) Η 4^ch2), -/^Vf 〆, FHHB (OH) 2 (3-176) Η HH Β· (Ο H) a (3-177) Η HHB (OH) 2 (3-178) Η HH (3-179) Η HH and DO (3-180) Η ^-(CH2h〇-^jl HHB (OH) a ( 3-181) Η -h(CH2)e^y HHB (OH) a (3-182) Η HHB (OH) j (3-183) Η HH Κι (3-184) Η -Hch2),h(X ^ HHB (OH) a 32 324142 201245173 No. R1 1 R12 R1 3 R1 4 Xa (3-185) Η HHB (OH) 2 (3-186) Η ^ch^-€〇HH (3-187) Η HH Sn (n-C4He) 3 (3-188) Η -S i (CH S) 3 HHB (OH) 2 (3-189) Η -S i (C2H5) 3 HHB (OH) 2 (3-190) Η -Si ( i -C3Hr) 3 HHB (OH) 2 (3-191) Η —Si (CH 3 ) 2 ( t — c,h9) HH (3-192) Η -S i (CH3) 2 (n -CeHI3) HH (3-193) Η -S i (CHa) 2(nC 1 2 H 2 s〉 HH Sn (n-C4He) 3 33 324142 201245173 No. R1 1 R 1 5 Rl 4 X2 (3-194) Η Η ch3 HB (OH) a (3-195) Η Η c2h5 HB (OH j (3-196) Η Η η — C β Η ! g HB (OH) a (3-197) Η Η n>CeHt3 H (3-198) Η Η η — C 1 2 Η a 3 H (3 -199) Η Η η —C82H4B H Sn (n—C4H9) a (3-200) Η π π - C β F &quot; HB (OH) 2 (3-201) Η Η och3 H (3-202) Η Η Ο ( n -C3Ht) HB (OH) 2 (3-203) Η Η Ο ( η — C β H tg ) HB (OH) B (3-204) Η Η Ο (η — CeFl3) H (3- 205) Η Η gas 〇 HB (OH) 2 (3-206) Η Η H Sn (n.-*C4Hg) g (3-207) Η Η HZ η B r (3-208) Η HM HM g B r (3-209) Η Η H .CO (3-210) Η Η n*C,13 H Κι (3-211) Η Η HB (OH) a (3-212) Η Η •w HB (OH) a (3-213) Η Η HB (OH) 2 (3-214) Η Η -) &lt;TF HB (OH) a (3-215) Η Η H (3-216) Η Η H a (n-C4Hfl) 3 (3-217) Η Ί Ί-^-〇(η-^Η13) HZ η B r 34 324142 201245173 R1 1 R1 2 R1 3 R 1 4 X2 (3-218) Η Η nC^n HB (OH) a (3-219) Η Η -Κχ. , · H (3-220) Η Η HB (OH) a &lt;3-221) Η Η -ΚΤ〇, · HB (OH) 3 (3-222) Η Η HB (OH)* (3-223) Η Si -Si (C Η3 ) , ( η -CI ο Η 2 1 ) HB (OH) 2 (3-224) Η Η HK right (3-225) Η Η -Hch2)6-QH Sn (n-CeHe ) 3 (3-226) Η Η 〆, FHB (OH) 2 (3-227) Η Η HB (OH) 2 (3-228) Η Η HB (Ο H) 2 (3-229) Η Η -hCH2fe -^jQ-F HB (OH) 2 (3-230) Η Η HB (OH) * &lt;3-23l) Η Η -SL (CH3) 3 HB (OH), (3-232) Η Η -Si ( i - C3 HT) 3 HB (OH) 2 (3-233) Η Η -Si (C Ha) 2 ( t -C *He) HB (OH) 2 35 324142 201245173 No. R1 1 R1 2 R1 3 R&quot; X2 (3-234) Η Η Η ch3 B (OH), (3-235) Η Η Η c2h5 K Right (3-236) Η Η Η i -CaH, Sn (n-C4Hg) 3 (3-237) Η Η η η — C 4 Η 9 B (OH) 2 (3-238) Η Η Η NB (OH) a (3-239) Η Η Η π — C β Η 1 a B (OH) 2 (3- 240) Η Η . Η n - C 1 2 Η 2 β (3-241) Η Η η η ~ ^ 1 5 Η 3 1 B (OH) 2 (3-242) Η Η η η - C i. β 3 β B (OH) a (3-243) Η Η η η ~ C β F ! 3 B (OH) 2 (3-244) Η Η Η η — C 1 2 F 3 5 B (OH) 8 ( 3-245) Η Η Η 〇 C2Hs (3-246) Η Η Η Ο U-CeH, 3) B (OH) 2 (3-247) Η Η Η Ο ( η — C ι 〇Η 2 !) S n ( n — C 4 H g ) 3 (3-248) Η Η Η 〇 (π. A C 〇Ρ 1 g ) B (OH) 3 (3-249) Η Η Η Ό M g B r (3-250 Η Η Η Z η B r (3-251) Η Η Η caH5 B (OH) „ (3-252) Η Η Η B (OH) 2 (3-253) Η Η Η (3-254) Η Η Η (3-255) Η Η Η B (OH) 2 (3-256) Η Η Η B (OH) a (3-257) Η Η Η -|-^-〇CHs B (OH) 2 (3- 258) Η Η Η B (OH) a 36 324142 201245173 No. R 1 1 R 1 2 R1 3 R 1 * X2 (3-259) Η Η Η n-Crf=13 B (OH) 2 (3-260) Η Η Η -ΚΤ〇, 咖(3-261) Η Η Η B (OH) 2 (3-262) Η Η Η • hcHd-Q Sn (n-C4He) s (3-263) Η Η Η B ( OH) 2 (3-264) Η Η Η B (OH) i (3-265) Η Η Η -Si (C Hs) a B (OH) 2 (3-266) Η Η Η -S i (CaH, ) a B (OH) 2 (3-267) Η Η Η -Si ( i -C3H7) 3 B (OH) a (3-268) Η Η Η -Si (C H3) 2 ( t - c4hj B (OH) 2 No. R1 1 R 1 2 R 13 R 1 4 X8 (3-269) ch3 CHg CHg HB (OH) 3 (3-270) C2H5 c2h5 C 3 H 5 H (3-271) n-CaHr n -CaHT n-C3Hr H Sn (n-C4Hq) 3 (3-272) n - C β Ha a n. — C ^ H j 3 Π ~ C (j H j 3 HB (OH) 2 (3-273) n — Ci2H2s Λ _ C 12^25 nC ! 2 H2 5 HB (OH) a (3-274) ch3 n _ ^ 12^25 ch3 HB (OH) 2 (3-275) HC Hs c h3 HB (OH) 2 (3-276) H n — C « H ^ 3 tl - O 5 HJ 3 HB (OH) 2 (3-277) OC Ha 〇c h3 〇ch3 H (3-278) O ( n - C 3 H r&gt; O ( n - C 3 H r) O ( n - C 3 H r) HB (OH) a (3-279) och3 H 〇ch3 HB (OH) 7 (3-280) 〇CHa n — C 〇 H i 3 〇ch3 HB (OH) 2 The wavy line of Table 1 refers to a bonding bond. Specific examples of the preferred aromatic compound (3) are, for example, numbers (3-1), (3-2), (3-3), (3-6), (3-8), (3-11). , (3-13), (3-15), (3-16), (3-17), (3-20), (3-21), (3-24), (3-26), ( 3-29), 37 324142 201245173 (3-32), (3-42), (3-43), (3-44), (3-45), (3-46), (3-47), (3-48), (3-49), (3-50), (3-51), (3-52), (3-54), (3-56), (3-57), (3 -59), (3-60), (3-61), (3-62), (3-63), (3-64), (3-65), (3-66), (3-67 ), (3-68), (3-69), (3-70), (3-71), (3-72), (3-73), (3-74), (3-75), (3-76), (3-77), (3-78), (3-79), (3-80), (3-81), (3-83), (3-84), (3 -85), (3-86), (3-87), (3-88), (3-92), (3-95), (3-96), (3-97), (3-98 ), (3-99), (3-100), (3-101), (3-103), (3-104), (3-105), (3-107), (3-109), (3-110), (3-112), (3-114), (3-124), (3-128), (3-129), (3-134), (3-135), (3 -137), (3-138), (3-139), (3-143 ), (3-147), (3-149), (3-151), (3-156), (3-159), (3-164), (3-169), (3-177), (3-196), (3-197), (3-198), (3-201), (3-203), (3-205), (3-207), (3-208), (3 -210), (3-219), (3-225), (3-228), (3-234), (3-235), (3_237), (3-239), (3-246), (3-249), (3-251), (3-253), (3-259), (3-269), (3-270), (3-271), (3-272), (3 -274), (3-276), (3-278), and (3-280). More preferred examples are number (3-1), (3-2), (3-3), (3-6), (3-42), (3-43), (3-44), (3) -45), (3-46), (3-47), (3-48), (3-49), (3-50), (3-51), (3-52), (3-54) ), (3-56), (3-57), (3-59), (3-64), (3-73), (3-78), (3-80), (3-92), (3-95), (3_101), (3-103), (3-104), (3-105), (3-107), (3-109), (3-110), (3-112) ), (3-114), (3-124), (3-128), (3-129), (3-156), (3-196), (3-197), (3-269), (3-272), (3-274) 324142 38 201245173 * and (3-276). * In the case where X2 of the aromatic compound (3) is a group represented by the formula (6), the condensation reaction is carried out, for example, in the presence of a transition metal catalyst and a base, for example, in a temperature range of from 〇 ° c to 150 ° C. The reaction can be easily carried out in a solution. As the transition metal catalyst used in the present condensation reaction, for example, a palladium catalyst or a nickel catalyst. As the palladium catalyst, a commercially available one can be used, and a palladium compound and a phosphine compound can be used in advance to prepare a palladium compound, and a palladium compound and a phosphine compound can be prepared in the present condensation reaction system. As a palladium catalyst, for example, ruthenium (triphenylphosphine) palladium (0), bis(acetic acid) bis(triphenylphosphine)palladium (II), bis[1,2-bis(diphenylphosphino)ethane] Palladium (0), [1,2-bis(diphenylphosphino)ethane]palladium(II) dichloride, dibromobis(triphenylphosphine)palladium(ruthenium), dichlorobis(dimethylbenzene) Palladium (II), dioxobis(methyldiphenylphosphine)palladium(II), dichlorobis(tricyclohexylphosphine)palladium(II), dioxobis(triethylphosphine)palladium(II) ), dioxane (triphenylphosphine) palladium (II), dichlorobis [ cis (2-nonylphenyl) phosphine] palladium (II), hydrazine (methyl diphenyl phosphine) palladium (ruthenium), Indole (tricyclohexylphosphine) palladium (0) and dichlorobis (1,1'-diphenylphosphinoferrocenyl) (II). As the palladium compound, for example, tris (dibenzyl ideneacetone) dipal ladium, ginseng (dibenzylideneacetone) dipalladium (0) chloroform adduct, palladium acetate ( II), gasified palladium (Π), (bicyclo [2. 2. 1] hept-2,5-di-diluted) monochlorination (II), (2, 2'-linked ratio bite base) Ίε, bis(acetonitrile) gas nitro (II), bis(benzonitrile)palladium(II) chloride, bis(acetonitrile)palladium (π), two gas (1 ,5_cyclooctadiene)palladium(II), dichloro(ethylenediamine)palladium(Π), dichloro(Ν,Ν,Ν,Ν,一324142 39 201245173 tetramethylenemonoamine) II), dichloro (1,10-phenanthroline) palladium (π), palladium (II) ethyl acetonide, palladium bromide (11), palladium (II) hexafluoroacetone acetone, palladium iodide ( II), palladium nitrate (11), palladium sulfate (11) and palladium (II) trifluoroacetate, preferably palladium acetate (ruthenium), palladium chloride (π) and tris(dibenzylideneacetone) dipalladium ( 0). These palladium compounds can be used commercially. As a phosphine compound, for example, trisylphosphine, ginseng (2-methylphenyl)phosphine, ginseng (3-methylphenyl)phosphine, ginseng (4-methylphenyl)phosphine, ginseng (pentafluorophenyl) Phosphine, ginseng (4-fluorophenyl)phosphine, ginseng (2-hydroxyphenyl)phosphine, ginseng (3-indolylphenyl)phosphine, ginseng (4-methoxyphenyl)phosphine, ginseng 2,4,6-trimethylphenyl(3-chlorophenyl)phosphine, cis(4-phenylphenyl)phosphine, tri-n-butylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, anthracene , 2_diphenylphosphinoethyl m diphenyl sulfanyl propane, 1,4-diphenylphosphinobutane, 12-dicyclohexylphosphinoethane, 1,3-dicyclohexylphosphinopropyl ,], [dicyclohexylphosphinobutyrate, bis-decylphosphinoethyl m dimethylphosphinopropane, u-dimethyl squarate, 1,2-diethylphosphinoethane , 13-diethylphosphinopropane, diethylphosphinobutane 'diisopropylphosphinoethane, diisopropyl: propyl propane L 4 - isopropyl phosphinobutane, 3 - 2 Phosphine, 2, (dicyclohexylphosphino)biphenyl, 2-(di-tert-butylphosphino)biphenyl, 2_ylendyl "2' 'methylbiphenyl, 2-(dicyclohexylphosphino) -2 -6, _2; keto 1,1'-biphenyl, 2-(dicyclohexylphosphino)-2, -(N, succinylamine, 'biphenyl, 2~ dicyclohexylphosphino _2, _mercapto-biphenyl, 2_(dicyclohexyl), 2'4,6'-triisopropyl u, _biphenyl, u, bis(phosphinyl)ferrocene and U _ bis(diisopropyl scaly) ferrocene phosphine compounds, which can be used by (4) commercially available, can be made according to the conventional method 324142 201245173. The amount of phosphine compound used, palladium compound 1 mole In general, a ratio of from 0.5 moles to 10 moles, preferably from 1 mole to 5 moles, is used as the recording medium used in the condensation reaction, for example, dioxane (1 1,_diphenyl) Phosphonoferrocenyl) nickel (II), dioxobis(diphenylphosphino)nickel(II), nickel (II) vapor and nickel (II) diiodide. Use of transition metal catalyst For the aromatic compound (3) 1 mol, the conversion metal is, for example, a ratio of 0.0005 mol to 0 5 mol. The condensation reaction is preferably carried out in a solvent, and as a solvent, for example, benzene or benzene. And aromatic hydrocarbons such as xylene; diacetyl, tetrahydroseven, two An ether such as an alkane, a tert-butyl decyl ether or an ethylene glycol dimethyl ether; a decylamine such as N,N-dimethyl decylamine or N,N-dimercaptoacetamide; dimethyl hydrazine; N_曱; ; and water. The reaction solvent may be used singly or in combination of two or more. It is preferably used after degassing, and 'the compound which is responsive to (4) may be partially dissolved or suspended in the reaction solvent. After that, the amount of the nitrogen gas is used to the aromatic heterocyclic compound (2a), and the weight of the degassing reaction is doubled to the weight ratio, preferably 2 times by weight (four) of the condensation reaction, preferably in the presence of a base. Such as lithium hydroxide, sodium argon oxide, potassium hydroxide, hydrogen child line # for the test 'example 曱 oxidation clock, sodium methoxide, oxidative unloading, ethoxy 1 it, nitrogen oxide lock, ethoxylated m sodium, the first Tributoxide ^' Na, carbonic acid oblique, carbonic acid sharp, strontium carbonate, carbonic acid charcoal ^ sodium carbonate and disc. (4) The amount of the material, the material ^ hydrogencarbonate unloading, Lin 't compound (3) 1 Mo Er and 324142 41 201245173 saying 'at least 0.5 moles ratio, preferably at least 1 mole ratio. The present condensation reaction can be carried out as a phase transfer catalyst in the presence of a phase-transfer catalyst, such as tetraalkylammonium halide, tetraalkylammonium hydrogen sulfate, and tetraalkylphosphonium oxide. The ammonium salt is preferably, for example, a tetra-n-butyl functional group and a benzyltriethyl ammonium chloride. The reaction atmosphere may be in the atmosphere. However, in order to prevent deterioration of the catalyst to be used, it is preferably carried out under an inert gas such as nitrogen or argon. The reaction temperature of the present condensation reaction can be, for example, 〇(3(: to 15). The range of rc can be, for example, a range of 1 minute to 96 hours.

To compound (4). The circulating coagulating material (4) method can be obtained. The reaction time of this condensation reaction, the circumference. After the end of the condensation reaction, an aqueous solution of ammonium hydride is used, and if necessary, the chemical cooperation represented by the horns (4-1) to (4-445) in Table 446) to (4-452) is compound (4), for example, The compound shown in Table I and the number (4) described later.

324142 42 201245173 ’ [Table 2]

No. R 1 Z 1 z 2 R&quot; R1 2 R 1 3 R 14 (4-1) CHg ss HHHH (4-2) ch3 ssc h3 HHH (4-3) c h3 ss c2h5 HHH (4~4) ch3 ssi - C 3 He HHH (4-5) ch3 ss Π — C 4 H g HHH (4-6) ch3 ssn — C β H ! 3 HHH (4-7) CH3 ss π-〇4Ηβ C^Hs HHH (4 -8) ch3 ssn ~ C t 2 H 2 5 HHH (4-9) c h3 ssn — C i β H 3 3 HHH &lt; 4-10) CHS ssn — C e F i 3 HHH (4-11) CaH0 Ss C h3 HHH (4-12) c 2 H5 ss C 2 H 5 HHH (4-13) c2h5 ssi - C 3 Hft HHH (4-14) CaHe ssn — C g H ! i HHH (4-15) c2H5 Ssn — C 】β H 3 3 HHH (4-16) n — C β ^ j 3 ss C h3 HHH (4-17) n — C eHla ssn — C e H la HHH (4-L8) n - C i 〇H 2 1 ssn - C β H ! 3 HHH (4-19) n — C 1 〇H 2 1 ssn — C 8 H i 7 HHH (4-20) n ~ C 1 0 H 2 1 ssn — C i 2 H aa HHH (4-21) n — C 2 〇H 4 1 ssc h3 HHH (4-22) n — C a ο H * 1 ss tl _ C g H j 3 HHH (4-23) n — C 2 〇H 4 1 ssn — C a H , THHH 43 324142 201245173

Compilation R 1 z 1 z 2 R1 1 R1 2 Rl 3 R &quot; (4-24) ch3 so HHHH (4-25) c h3 so C h3 HHH (4-26) CH, son - C β H ja HHH (4-27) C h3 so π — C e F is HHH (4-28) ch3 s S e HHHH (4-29) ch3 s S e C H9 HHH (4-30) ch3 s S en - C β H ! g HHH (4-31) ch3 S e SHHHH (4-32) ch9 S es C Ha HHH (4-33) CH, S esn - C β H ! a HHH (4-34) c h8 s S en — C e F ta HHH &lt;4-35) CHS s S OC Ha HHH (4-36) ch3 ss O (n -c 3H 7) HHH (4-37) ch3 ss O ( n - C β H,,) HHH (4-38) ch3 ss O ( n - C , F , 3) HHH (4-39) ch3 so O ( n - C „ H, 3) HHH (4-40) CHg s S e O ( n - C 8 H, T) HHH (4-41) ch3 ss HHH (4-42) ch3 ss HHH (4-43) ch3 ss HHH (4-44) ch3 ss HHH (4-45) CH, ss 13 HHH ( 4-46) c h3 so HHH (4-47) ch3 so |~Q-rvCeH13 HHH (4-48) CH, s S e HHH &lt;4-49) CHa s SHHH 44 324142 201245173 No. R 1 Z 1 z 2 Rl 1 R&quot; R13 R 1 4 (4-50) C Η 3 S s -HJT Η Η Η (4-51) CHa ss Η Η Η (4-52) C h3 ss Η Η Η (4-53) ch3 so -H〇T Η Η Η (4-54) ch3 s S e S , n-CeHi3 -\\X Η Η Η (4-55) ch3 ssj~C〇~C8Hi7 Η Η Η (4-56) ch9 ss - shouting F Η Η Η (4-57) CH ss Η Η Η (4-58) CH ass Η Η Η (4-59) CHa ss Η Η Η (4-60) CHa so '^〇&gt;_ocHs Η Η Η (4-61) ch3 s S e Η Η Η (4-62) CHa ss Η Η Η (4-63) CHa so Η Η Η 45 324142 201245173

No. R 1 z 1 z 2 R1 J R1 2 R 1 3 R 14 (4-64) ch3 s S e HHH (4-65) ch3 S Θ s HHH (4-66) CHg ss Heart 7 HHH (4-67 Ch3 ss -S i (CH,) 2 ( n. -cbh17) HHH (4-68) ch3 ss -|-(ch2)hQ HHH (4-69) CH 3 ss Ή W n&gt;CeH 13 HHH (4 -70) CHg ss FFHHH (4-71) CHg so HHH (4-72) ch8 s S o -Η〇Η2) ί-^ HHH (4-73) CH, ss HHH &lt;4-74) CHg ss HHH (4-75) ch3 ss -Hchj)s-^QHHH (4-76) c h3 S e S e -Hch,)«C〇HHH (4-77) ch3 SS -Si ( CH g· ) s HHH ( 4-78) ch3 SS -Si (CaH„) a HHH (4-79) CH, SS -Si ( i -C 3 H7 ) a HHH (4-80) ch9 s S -S i (CH3) j ( t -c4h9) HHH 46 324142 201245173

No. R 1 z 1 2 2 R 1 1 R12 R 1 3 R ie (4-81) CHa ss HC Ha HH (4-82) CH 3 ss H c2 h5 HH (4-83) CH 3 ss H n - C a He HH (4-84) CHa ss H i -C a He HH (4-85) CHa ss H n — C * Η e HH (4-86) ch3 ss H s - C 4 H9 HH (4-87 CHa ss H n - C s H ! t HH (4-88) C Hs ss HHH (4-89) ch3 ss H n — C β H i 3 HH (4-90) CHg ss HHH (4-91) Ch3 ss H Q2H5 HH (4-92) CHa ss H n - C τ Η , e HH (4-93) CHg ss H λ - C 8 H jy HH (4-94) CHg ss H n — CH j fl HH (4-95) ch3 ss H n — C 】0 H 2 1 HH (4-96) ch9 ss H n-CeHi7 n-CeHts HH (4-97) ch3 ss H n — C i 1 H 2 3 HH ( 4-98) ch3 ss H n - C i 2 H 3 3 HH (4-99) ch3 ss H &quot;^-η-ΟβΗ13 rvCeHu HH (4-100) ch3 ss H n — C i 3 H 2 7 HH (4-101) CH9 ss H n C j 4 H 2 〇HH (4-102) CH9 ss H n* — C ! 5 H 3 1 HH (4-103) ch3 ss H n - C j β H a 3 HH (4-104) CHg ss H n - C i 7 H 3 e HH (4-105) ch3 ss H n — C 1 BH 3 τ HH (4-106) ch9 ss H 11 —CiflH3e HH (4-107 ) CHg ss H n — C 2 〇H * ! HH (4-108) ch3 ss H n —C22H4e HH (4-109) CHa ss H Π - C 2 g H 5 ! HH (4-110) CHS ss H n— HH (4 -111) ch3 ss H n -C a 〇He t HH (4-112) ch3 ss H λ - C e F , a HH (4-113) CHa ss H n _ C 8 F tr HH (4-114) Ch3 ss H n _ C 1 2 F 2 5 HH 47 324142 201245173

No. R 1 z 1 z 3 Rl 1 R 1 2 R 13 R “ (4-115) C2H0 ss HHHH (4-116) c2hs ss H c h3 HH <4-117) c3h5 ss H CaH5 HH (4-118) C 2 H5 ss H i -C 9 H9 HH (4-119) ca hb ss H n -C 4 He HH (4-120) He ss H n - C 5 H , ! HH (4-121) CaH5 ss H ~ HH (4-122) CaHs ss H n - C β H ta HH (4-123) c, h5 ss H n-CiHi C2H5 HH (4-124) c2h5 ss H n. 0 8 H j 7 HH (4 -125) c2h8 ss H n - C 1 〇H 2 ^ HH (4-126) CaHe ss H n*CeHi5 HH (4-12?) c2hs ss H-CiaH28 HH (4-128) c3h5 ss H n-CeH ^ n-CeHu HH (4-129) c,h8 ss H nC ! eH g 3 HH (4-130) c2h5 ss H 11 ~ CJ 〇H 4 JHH (4-131) CflHs ss H n - C 2 β Η 5 ! HH (4-132) n — C 4h0 ss HHHH (4-133) a C *Hfl ss H ch9 HH (4-134) n — C tHg ss H c2h, HH (4-135) n — C « Η, ss H n — C 4 H e HH (4-136) n C *Hg ss H Λ - C a H jj HH (4-137) n — C 4Hg ss H Π. ~ C 8 H j 7 HH ( 4-138) n - C 4H0 ss H n - C ja H 2 5 HH (4-139) n. ** C «Ηβ ss H n - C ja H 3 3 HH 48 324142 201245173 No. R 1 Ζ 1 ζ 2 R 1 1 R13 R 1 3 R 1 4 (4-UO) n — C β Η ! a SS Η Η Η Η (4-141) η — C βΗχ 3 SS Η C η3 Η Η (4-142) η — C «Η, 3 SS Η Λ 一 C β Η ι 3 Η Η (4-L43) η — C βΗ, 3 SS Η H — 0 g Η 1 7 Η Η (4-144) η — C 8^17 SS Η Η Η Η (4-145) η — C 8^17 SS Η C2Hs Η Η (4-146) η — C 8η17 SS Η η — C β Η 1 3 Η Η (4- 147) η — C aH17 SS Η η — C 8 Η ! 7 Η Η (4-148) η — C 1 〇Η 2 1 SS Η Η Η Η (4-149) η - C 1 〇Η 2 1 SS Η C η3 Η Η (4-150) n — C 1 〇Η 2 1 SS Η η - C β Η χ 3 Η Η (4-151) η - C ι ο ^ β 1 SS Η π ~* C a Η ^ 7 Η Η (4-152) η — C t 〇Η 2 1 SS Η 11 — C ι 2 Η 2 s Η Η (4-153) η - C ί 0 Η 4 SS Η Η Η Η (4-154) η. — C 2 〇Η 4 1 SS Η ch3 Η Η (4-155) η — C 2 0^4 1 SS Η η - C β Η ! g Η Η (4-156) η. — C a 〇Η 4 1 SS Η η — 0 s ^ ι 7 Η Η (4-157) η — C a 〇Η 4 1 SS Η n — C12H25 Η Η 49 324142 20124517 3

No. R 1 Z 1 2 2 Rl 1 R12 R 13 R 14 (4-158) CHS s 〇H CHg HH (4-159) ch3 s 〇H n - C « H ja HH (4-160) CHa s 〇 H n — C a H tr HH (4-161) CH3 s 〇H n^CiiHae HH (4-162) CHS s 〇H π — C e F : 3 HH (4-163) ch3 so H n — C 8 F i τ HH (4-164) CHS so H Cia^as HH (4-166) CHa s S e H CHg HH (4-167) CHg s S e H n - C β H : 3 HH (4-168 ) ch9 s S e H n - C β H j THH (4-169) CHa s S e H n. — CiaHae HH (4-170) ch3 S e SHHHH (4-171) ch3 S e SHC Ha HH (4 -172) ch3 S es H π ~ 0 β H j 3 HH (4-173) CHS S es H n - C 8 H if HH (4-174) ch3 S es H n — C 1 2 H 2 BHH (4 -175) CHa SS 6 H n - C e F &quot; HH (4-176) CHa SS θ H n - C 8 F ! THH (4-177) ch3 S s H 〇ch3 H - H (4-1T8) CHa S s H oc2h9 HH (4-179) CHS S s HO (n-CaHT) HH (4-180) CHg S s HO { n - C 4 Hfl) HH &lt; 4-181) ch3 S s HO ( n - CB H ,,) HH (4-182) CHa S s HO (nC, H13) HH (4-183) ch3 S s HO (n-CTHl5) HH (4-184) ch3 S s HO (n-CeH1T ) HH (4-185) CHS S s H 〇 &lt;n-Cl0H2i) H H 50 324142 201245173

No. R 1 z 1 z 2 Rl 1 R&quot;R&quot; R 14 (4-186) CHa ss HO ( n - C t 8 H28 ) HH (4-187) CH 3 ss H Ο (η. — CjeH33) HH ( 4-188) ch3 ss H 〇( Ϊ1 — C is ^ 3 T ^ HH (4-189) CHS ss HO (n — Cz〇H*i) HH (4-190) ch3 ss HO (11.-024^ 49) HH (4-191) ch3 ss H 〇(n_C28H5r) HH (4-192) ch3 ss H 〇( n _ C 3 Η e !) HH (4-193) ch3 ss H 〇 ( n- Ce F l3 HH (4-194) ch3 ss H 〇 ( tl - C 8 F if ) HH (4-195) ch3 ss H 〇 (n — C12F23) HH (4-196) CHa so HO ( n - C, H , 3) HH (4-197) ch3 so H 〇(n-CaH1T) HH (4-198) CH3 so HO (n-Ci2H25) HH (4-199) CHa s S e HO ( n - Ce H , 3 ) HH (4-200) CH 9 s S e H 〇( n - Ca H &quot;) HH (4-201) CHa s S e H 〇(n~*〇i2^25^ HH (4-202) ch3 ss H -\~o HH (4-203X ch3 ss HHH (4-204) ch3 ss HHH (4-20S) CHa ss HHH (4-206) ch3 ss HHH (4-207) CHa ss H nC^i3 HH ( 4-208) ch3 ss H n-CyH17 HH (4-209) CH3 ss HHH (4-210) ch3 ss H n-C12H25 HH (4-211) ch3 ss H fear H33 H H (4-212) ch3 s s H n-CiHfi Π-〇4Ηβ H H 51 324142 201245173

No. R 1 Z 1 z 2 R 1 1 R13 R 1 3 R 14 (4-213) ch9 S s HFFHH (4-2(4) ch3 S s H -iQ-rvCi,, HH (4-215) ch9 so HHH (4 -216) ch3 so HHH (4-217) CHa so H rvCeHn HH (4-218) CHa so HHH (4-2L9) ch3 s S e HHH (4-220) CH 9 s S e H -\&lt;y ^ HH &lt;4-221) ch3 s S e H -h^^-rvC4He H. H (4-222) ch3 s 5 e HHH (4-223) CHa s SHHH (4-224) CHS ss H -KT0&quot ;·HH (4-225) CHa ss H -kJ HH (4-226) CHS ss HHH (4-227) CHg ss H -KT HH (4-228) ch3 ss H -Hi HH (4-229) CHa Ss HS^/n_ceFl3 -KT HH 52 324142 201245173

No. R 1 Z 1 z 2 R 1 1 R 1 2 R 1 3 R 14 (4-230) ch3 ss H -1&lt;TF HH (4-231) CH aso HHH &lt;4-232) CHa so H w HH (4-233) ch3 so H w HH (4-234) ch3 s S e HHH (4-235) ch3 s S e HHH (4-236) ch3 s S e H KT HH (4-237) ch3 s SH ^\XVC8Hi7 HH &lt;4-238) ch3 ss HFHH (4-239) CHa ss HHH (4-240) ch3 ss HHH (4-241) ch3 ss H -|-'^^-〇(n-C3H7) HH (4-242) ch3 ss H -Ι-^3_0(η'°44,) HH (4-243) ch3 ss HHH (4-244) CHa ss HHH 53 324142 201245173

Compilation R 1 Z 1 z 3 R 1 1 Ria R 1 3 R 1 4 (4-245) CHS S s HHH (4-246) CHa ss HHH &lt;4-247) CH, ss HHH (4-248) CH, ss H ^〇(n-CeHii 〇(n-CeHiJ HH (4-249) ch3 ss H -i〇v W n-CVis HH (4-250) ch3 so H -^〇-°CH3 HH &lt; 4-250 ch3 s 0 H -|-^^-〇(n-C4Hg) HH &lt;4-252) ch3 so HHH (4-253) CH3 s S e H -l-^-OCHs HH (4-254 CHa s S e H ^^3_〇(η'〇3Η7) HH (4-255) ch3 s S e HHH (4-256) CHa ss H -Kx〇,, HH (4-257) ch3 ss H -H〇T〇, nW, HH (4-258) ch3 ss HHH (4-259) CH3 ss H -i&lt;r°'n'Ci〇Ha HH (4-260) CHa ss HHH (4-261) CH3 so HHH 54 324142 201245173

No. R 1 z 1 z 2 R1 1 R12 R&quot; R 1 4 (4-262) CH as S 0 H -i^T°'n'c,eH3S HH (4-263) ch9 S es HHH (4-264 CH ass H &lt;3T〇Wl7 HH (4-265) c h3 s S e H •, 峨HH (4-266) ch3 ss HHH (4-267) ch3 ss H -Si (C Ha) 2 ( η - C 8 H ! 7 ) HH (4-268) c h3 ss H —Si (CH3)2 (n — C i ό H 2 1 ) HH (4-269), c h3 ss HHH (4-270) Ch3 ss HHH (4-271) CHa ss H 4-&lt;ch2)b-^ HH (4-272) C Ha ss HHH (4-273) CHa ss HHH (4-274) C Hg ss H -|- (CH 2)4-^^-fl-CeHi3 HH (4-275) ch3 ss HFFHH (4-276) C Hg ss H - Bu (4)·〇HH (4-277) C h3 so HHH (4-278) Ch3 s S e H such as cha^QHH (4-279) CHa ss HHH (4-280) CHa s S Θ H -Hch2u-^j1 HH 55 324142 201245173

Compilation R 1 Z 1 z 2 R 1 1 R 1 2 R 1 3 R 1 4 (4-281) ch9 ss HHH (4-282) ch3 ss H - Bu ("^2 heart HH (4-283) ch3 Ss HHH (4-284) ch3 ss HHH (4-285) ch9 ss H -hcF2).-^j] HH (4-286) CHa ss H, even. Willow HH (4-287) ch3 ss H -h^-ζχ^ HH (4-288) ch3 ss H -Hch2)bh(jQ^-f HH (4-289) CH 3 ss HHH (4-290) ch3 S Θ S e H -Hch2),2^]QHH (4-291) ch3 ss HHH (4-292) CHa ss H -Si (C Ha) 3 HH (4-293) ch3 ss H -Si (C zH5 a HH (4-294) ch3 ss H -Si ( i -C3Ht) 3 HH (4-295) ch3 ss H -Si'(CH3)2 (tC 4 Hg ) HH (4-296) ch3 ss H — S i (CHa) 2 (n — CeH13) HH (4-297) CHg ss H — Si(CH3}2(n — C ia H 2 B ) HH 56 324142 201245173

No. R 1 z 1 z 2 R 1 1 R&quot; R 1 3 R 1 4 (4-298) ch3 ss HHC Ha H (4-299) ch3 S s HH c3h5 H (4-300) c h3 S s HH λ ~ C β H xa H (4-301) CH 3 ss HH n-C8H17 n*CeH13 H (4-302) C Ha ss HH n — C 1 2 H 2 5 H (4-303) ch3 ss HHH ( 4-304) ch3 ss HH n - C β F ! 3 H (4-305) CaH5 ss HHHH (4-306) C2H5 ss HH n — C 4 H g H (4-307) C 2 H sss HH n- C8H1T H (4-308) C*H5 ss HH rvCgHi; n-C0Hl3 H (4-309) n — C . 6^13 ss HH n — C β H l 3 H (4-310) n — C 8^ 17 ss HH n — C 8 H i 7 H (4-311); n - C 1 〇H 2 1 ss HH n - C β H ! a H (4-312) n. ~ C i 〇H a 1 ss HH n - C 8 H i TH (4-314) ch9 so HHC h3 H (4-315) CH 3 so HH π C β H i 3 H (4-316) ch3 so HH π _ C 8 H i 7 H (4-317) ch3 so HH n - C ^ 2 H a 3 H (4-318) ch3 so HH n - C e F i 3 H (4-320) ch3 s S e HH c h3 H (4-321 CHa s S e HH Π — C g H x 7 H (4-323) ch3 S e SHH n - C β H i 3 H (4-324) ch3 SS e HH n- - C 8 F i 7 H ( 4-325) CHg ss HH . och3 H (4-326) C H 9 s s H H O ( n - C 3 H r) H (4-327) CHg s s H H O (n-CeH13) H 57 324142 201245173

No. R 1 z 1 z 2 R&quot; R12 Rl 3 R 1 4 (4-328) ch3 ss HHO ( n - C 0 F , 3 ) H (4-329) CH 3 so HHO ( n - C 8 H , 7 H (4-330) ch3 s S e HHO ( n - C , H , a ) H (4-331) ch3 ss HH -i &lt;3 H (4-332) ch3 ss HH -H0^3 H (4 -333) ch3 ss HH -丨H &lt;4-334) ch3 ss HH ~|~^y~n-CSH13 H (4-335) ch3 s 5 HHFFH (4-336) ch3 s SHHH (4-337) Ch3 so HH -iO H (4-338) ch3 s 0 HHH (4-339) ch3 s S e HHH (4-340) ch3 s S e HHH (4-341) CHa ss HH _丨H (4-342 Ch3 ss HH -hDT·5 H (4-343) CHa ss HH heart, s H (4-344) CHg ss HH -ktf H (4-345) ch3 so HHH 58 324142 201245173

No. R 1 Z 1 z 2 R &quot; R12 R 1 3 R 1 * (4-346) CHS so HHH (4-347) CHa s S e HHH (4-348) CHa s S θ HH -KJ H &lt; 4-349) CH3 ss HH &quot;^O〇~CrfHir H (4-350) CHa ss HH -|-^^-〇ch3 H (4-351) CHa ss HH -|-^^-〇(n- CeH,3) H (4-352) CHa ss HH -!〇, n-CeF,s H (4-353) CHa so HH -i-^^-〇(n-c4hw · H (4-354) ch3 s S e HHH (4-355) ch3 ss HH -KT0, (4) H (4-356) ch3 ss HHH (4-357) ch8 s S e HHH (4-358) ch3 ss HH -KT, F17 H (4 -359) CHS s S e HH KJ0, heterogeneous H (4-360) CHa ss HHH &lt;4-361) ch8 ss HH -Si (CH3)a(nC i ο H ai ) H 59 324142 201245173

No. R 1 z 1 2 fl R 1 1 R12 R13 R 1 4 (4-362) ch3 s SHH -i-tcHd-nQ H (4-363) ch3 ss HH -hcH2&gt;,^QH (4-364) ch9 Ss HHFFH (4-365) ch3 ss HHH (4-366) ch3 so HHH (4-367) ch3 s S e HH -hcH2)BQ H (4-368) ch3 s SHH -|ich2)-^j1 H ( 4-369) CHa s SHH 2)b 八工H (4-370) ch3 s SHH - 卜H (4-371) ch3 S e S e HH -hcn-H^QH (4-372) CHa SSHH -Si (CH a) 3 H (4-373) ch3 SSHH -Si ( i -CSHT) a H (4-374) ch3 S s HH -Si (CH8)2(tC H 60 324142 201245173 No. R 1 z 1 z 8 R 1 1 R 1 a R13 R14 (4-375) ch3 ss HHH c h3 (4-376) CH ass HHH Ca h5 (4-377) ch3 ss HHH i — C 3 H 9 (4-378) c h3 ss HHH n — C * H 9 (4-379) CHa ss HHH (4-380) ch3 ss HHH n - C β H ia (4-381) ch3 ss HHH n~C12H25 (4-382) ch3 ss HHH λ — C 1 5 H 3 x (4-383) ch3 ss HHH CteH3e (4-384) CHa ss HHH λ - Ce F ta (4-385) ch3 ss HHH n-C12F2S (4-386) n — C β H j 3 ss HHH n - C6 H t 3 (4-387) Λ — C 1 〇H 2 1 ss HHHH — CQM ^ g (4-388) n — C 1 〇H 2 lss HHH n — C ; 2 H 2 s (4-390) ch3 so HHHC Hg (4-391) ch3 so HHH ti - C e H ja (4-393) CH3 s S e HHH CHa (4-394) CH3 s S e HHH n — C β H j 3 (4-396) CH a S e SHHH π — C ο H ] 3 (4-397) CHg s S e HHH n - C a F 1 7 (4-398) CHa s SHHH OCaHs (4-399) ch3 s SHHHO (n-CeHls) (4-400) ch3 s SHHH 〇(It — 0 1 0 FI 2 l ) 61 324142 201245173 Compilation R 1 Z 1 za R 1 1 Ria R 1 3 R14 (4-401) CHa S s HHHO Uc, f13&gt; (4-402) C Hs so HHHO ( n - C„H,3 ) (4- 403) ch9 s S e HHHO (nC 8 Hl r) (4-404) CH ass HHH .-iO (4-405) ch3 ss HHH .|hQ_ch3 (4-406) CHa ss HHH -1hQ^C2H5 (4- 407) ch3 ss HHH -l〇-nJC "(4-408) CHa so HHH r&gt;-CeHi3 (4-409) CHg s S e HHH '〇) (4-410) CH 3 s SHHH (4-411) Ch3 s SHHH &lt;4-412) CHg s SHHH (4-413) ch3 ss HHH (4-414) ch3 so HHH Heart — (4-415) ch3 s S e HHH (4-416) CHg s SHHH (4 -417) ch3 s SHHH j&quot;^3&quot;~〇(n-ce H,d 62 324142 201245173 No. R 1 z 1 za R &quot; Ria R13 R 1 4 (4-418) CHa ss HHH (4-419) ch3 so HHH -|-^^-〇ch3 (4-420) c h3 s S e HHH -!-〇&gt;-〇(&quot;-〇»叶) (4-421) c h3 s SHHH heart. , (4-422) CHa so HHH - ", complement 7 (4-423) CH as S 9 HHH (4-424) ch9 S θ s HHH -ΚΤ〇,, 41 (4-425) ch3 ss HHH ( 4-426) ch9 ss HHH order (c is called *〇(4-427) ch3 ss HHH (4-428) ch3 ss HHH (4-429) ch8 S e S e HHH H-(CH2)1z-^Q ( 4-430> ch9 ss HHH -Si (CH,) 3 (4-431) ch9 ss HHH -Si (C 2 H5), (4-432) ch9 ss HH · H -Si ( i -C3H7) 3 (4 -433) ch3 ss HHH -Si (CH,) , ( t -C 4 Hs) 63 324142 201245173

No. R 1 z 1 z 2 R&quot; R12 R 1 3 R 14 &lt;4-434) ch3 ssc Ha c h3 ch3 H (4-435) C Η 3 ss c2 h3 CaH5 CaH5 H (4-436) ch3 ssn — C3 Hr n -C3 n — C 3 H 7 H (4-437) C Η 3 ssn — C β H isn — C 〇H ian — C β H 1 s H (4-438) CHS ssn — cl 3 H 2 5 n—C12H25 n - C ! 2 H 2 3 H (4-439) CH 3 ssc h3 n~Cl2H25 CHa H (4-440) CHS ss HC h3 CHa H (4-441) ch3 ss H π — C β H i 3 n - C β H xa H (4-442) ch3 ss 〇CHa 〇c h3 〇ch3 H (4-443) CH 3 ss O ( n - C s HT) 0 ( n - C 3 H r) 0 ( n - C 3 H r) H (4-444) CH ass OC Hs H OC Hs H (4-445) CHa ss och3 n — C β H i 3 〇CH 3 H The wavy line of Table 2 refers to the combination key.

Preferred specific examples of the compound (4) are, for example, numbers (4-1), (4-2), (4-3), (4-5), (4-6), (4-8), (4-10), (4-16), (4-17), (4-18), (4-24), (4-28), (4-31), (4-35), (4 -37), (4-41), (4-42), (4-49), (4-51), (4-52), (4-56), (4-57), (4-58 ), (4-68), (4-73), (4-81), (4-82), (4-83), (4-84), (4-85), (4-86), (4-87), (4-88), (4-89), (4-90), (4-91), (4-93), (4-94), (4-95), (4 -96) , (4-98), (4-101), (4-103), (4-107), (4-108), (4-110), (4-112), (4-113 ), 64 324142 201245173 (4-114), (4-122), (4-127), (4-137), (4-140), (4-142), (4-148), (4- 150), (4-159), (4-160), (4-161), (4-166), (4-167), (4-177), (4-178), (4-181) , (4-184), (4-186), (4-202), (4-203), (4-207), (4-212), (4-213), (4-223), ( 4-225), (4-228), (4-230), (4-239), (4-243), (4-246), (4-248), (4-257), 4-260), (4-269), (4-271), (4-279), (4-291), (4-298), (4-299), (4-300), (4- 302), (4-308), (4-314), (4-320), (4-321), (4-325), (4-327), (4-331), (4-332) , (4-334), (4-341), (4-344), (4-350), (4-362), (4-375), (4-376), (4-380), ( 4-381), (4-390), (4-393), (4-394), (4-398), (4-399), (4-404), (4-410), (4- 416), (4-434), (4-435), (4-436), (4-437), (4-439), (4-441), (4-442), (4-443) And (4-445) as shown. More preferred examples are numbers (4-1), (4-2), (4-3), (4-5), (4-6), (4-17), (4-18), (4- 35), (4-37), (4-81), (4-82), (4-83), (4-84), (4-85), (4-86), (4-87) , (4-89), (4-90), (4-93), (4-96), (4-98), (4-103), (4-112), (4-140), ( 4-142), (4-148), (4-150), (4-159), (4-167), (4-177), (4-178), (4-181), (4- 184), (4-202), (4-203), (4-207), (4-223), (4-225), (4-230), (4-239), (4-298) , (4-299), (4-300), (4-302), (4-308), (4-325), (4-327), (4-331), (4-332), ( 4-375), (4-376), (4-380), (4-381), (4-399), (4-437), (4-439), and (4-441). The condensed polycyclic compound (5) containing an oxygen group element can be obtained by reacting the compound (4) 324142 65 201245173 with an acid. Specific examples of the acid include, for example, a mixture of trifluoromethanesulfonic acid, acenaphthene, sulfuric acid, scaly acid, a mixture of acid and pentoxide, and hydrochloric acid. Preferred examples are trifluorofanesulfonic acid, sul alkanesulfonic acid, sulfuric acid and phosphoric acid. The acid to be used may be diluted with water or the like as needed. The compound (4) in the acid is directly or diluted with a solvent such as trichloromethane and placed in a reaction vessel, and stirred at a temperature of from -20 ° C to 10 ° C for 1 minute to 48 hours. reaction. At this time, a dehydrating agent such as phosphorus pentoxide may be present. After completion of the reaction, for example, the reaction mixture may be mixed with water, and the precipitated solid may be filtered and mixed with water, and if necessary, a solvent may be added to separate the organic layer or may be concentrated. If necessary, a condensed polycyclic compound containing an oxygen group element can be purified by a general purification method such as column chromatography, distillation, recrystallization, or recycle gel permeation (recycle gel permeation). ). Rust cation (can be treated with a multi-ring combination

Water mixed, over (four) φ... month reaction compound (4) after mixing with acid 'J water, = ^ intermediate, if necessary, in the presence of solvent rust cations, amines and other organic tests, in the 5 Add (4), 3B, for example, 1 minute to 4 8 hours. However, after, who: the temperature of the Buddha's point of the grain, can be searched by the tube_analysis method, the general fine, soil, mouth, day, cycle gel permeate (5) . 'Condensation Polycyclic Formula of Oxygen Group Element 324142 66 201245173 For example, the compound represented by the numbers (5-1) to (5-452) of the condensed polycyclic compound (5) containing an oxygen group element.

324142 67 201245173 [Table 3]

No. Z 1 z * R 1 1 R1 2 R 1 3 R 1 * (5-1) S s HHHH (5-2) S s C h3 HHH (5-3) S s c2h5 HHH (5-4) S si - C 3 Hg HHH (5-5) S s tl — C 4 H g HHH (5-6) S sn — C β H i 3 HHH (5-7) S s ^yn-C4l·^ QzHs HHH (5 -8) S sn - C12H25 HHH &lt;5-9) S sn* — C ie H 3 3 HHH (5-10) S sn ~ C „ F , 3 HHH (5-28) SS e HHHH &lt;5- 29) SS ec h3 HHH &lt;5-30) SS en - C β H i 3 HHH (5-31) S e SHHHH (5-32) S esc h3 HHH (5-33) S esn — C β H ia HH .H (5-34) SS en — C e F i3 HHH (5-35) SS 〇ch3 HHH (5-36) s SO ( n - C 3 H 7) HHH (5-37) s SO ( n — C β H ! 9 ) HHH (5-38) s SO ( n - C e F , 3) HHH (5-40) ss © 0 (n-C8Hir) HHH (5~41) ss HHH (5-42 ) ss - heart CH3 HHH (5-43) ss ~1~^~~^~Π-〇4Η9 HHH (5-44) ss HHH (5-45) ss ^~n-CaPi3 HHH (5-48) s S Θ -|-^^-η-〇4Ηβ HHH 68 324142 201245173

No. z 1 z 2 R 1 1 R1 2 R 1 3 R 1 4 (5-49) ss HHH (5-50) ss KT HHH (5-51) ss HHH (5-52) ss • 丨HHH (5- 54) s S e S^/rvCeHi3 -h〇t HHH (5-55) ss -Hj〇~CeHi7 HHH (5-56) ss - shout FHH -H (5-57) ss -|h^^-OCH3 HHH (5-58) ss -i-^^-Oin-Ce^a) HHH (5-59) ss -!〇0, W nC^13 HHH (5-61) s S e HHH (5-62) Ss - ◎ Ο, 3 HHH 69 324142 201245173

No. z 1 z 2 Rl 1 R1 2 R 1 3 R 1 4 (5-64) s S Θ HHH (5-65) S Θ s HHH (5-66) ss -KT0,·7 HHH (5-67) Ss -Si (C Η 3 ) a ( n -CaH 17) HHH (5-68) ss -|-(ch2)-QHHH (5-69) ss CH 2)4-^^^-n-CeHis HHH ( 5-70) s .s FFHHH (5-72) s S e HHH (5-73) ss -|-(ch2)-^J] HHH (5-74) ss HHH (5-75) ss -Hch^ -〇0 HHH (5-76) S e S θ -hcH2)l2(QHHH (5-77) S s -Si (C H3) 3 HHH (5-78) S s -Si (C2Hb) 3 .HHH ( 5-79) S s -Si ( i -C 3 H7 ) 3 HHH (5-80) S s -S i (CH3) 2 ( t -C4Hb) HHH 70 324142 201245173

Compilation z 1 z 2 R&quot; R1 2 Rl 3 R &quot; (5-81) ss H c h3 HH (5-82) ss H c2h5 HH (5-83) ss H n — C 3 HHH (5-84 ) ss H i - C a H9 HH (5-85) ss H n - C 4 Hg HH (5-86) ss H 5 - C 4 Hg HH (5-87) ss H n - C a H ! j HH (5-88) ss HHH (5-89) ss H n — ^ e ^ i 3 HH (5-90) ss H o HH (5-91) ss H nC^Hg P2H5 HH (5-92) ss H n - CTH , s HH (5-93) ss H n — C g H i 7 HH (5-94) ss H n — C g H ! 9 HH (5-95) ss H n — C i 0 H 2 i HH (5-96) ss H n-CeHi7 n-CeHi3 HH (5-97) ss H n — C ! i H z 3 HH (5-98) ss H n — C 1 2 H 2 3 HH (5 -99) ss H n'CeH&quot; rvCeHi3 HH (5-100) ss H n - C ja H2 7 HH &lt;5-101) ss H n — C 1 4 H 2 〇HH (5-102) ss H n ^ x 5 H 3 j HH (5-103) ss H n—C “H33 HH (5-104) ss H n — C 1 7 H 3 5 HH (5-105) ss H n — Ci8H37 HH &lt;5 -106) ss H n—Ci9H39 HH (5-107) ss H n — C 2 〇H * i HH (5-108) ss H n — C22H45 HH (5-109) ss H n - C a 5 H 5 t HH (5-110) ss H n-C28H57 HH (5- 111) ss H n.-Cs〇Hei HH (5-112) ss H n - C e F , 3 HH (5-113) ss H n _ C 8 F 1 7 HH (5-114) ss H n — Cl2F 20 HH 71 324142 201245173

No. z 1 z * R 1 1 R 1 * R &quot; R 1 4 (5-166) s S e H c h3 HH (5-167) s S θ H n _ C β H l 3 HH (5-168 s S e H n — C 8 M ^ 7 HH (5-169) s S e H n—C12H2S HH (5-170) S es HHHH (5-171) S es H ch3 HH (5-172) S Es H n - C β H 1 3 HH (5-173) S es H n C g H jr HH (5-174) S es H n — C12H23 HH (5-175) SS e H n — C e F ! 3 HH (5-176) s S e H n — C a F 1 7 HH {5-177) s SH OC h3 HH (5-178) s .s H oc2h5 HH {5-179) ss H 〇(n - C 3 H7) HH (5-180) ss H 〇(n -C4H,) HH (5-181) ss H 〇(n - C5 H t ,) HH (5-182) ss H 〇(n - Ce H ja ) HH (5-183) ss H 〇(n - C r H x 5 ) HH (5-184) ss H 〇(n - C8 H ! 7 ) HH &lt;5-185) ss H 〇(n —Ci〇H2i) HH 72 324142 201245173

No. z 1 z 2 R1 1 Rlz R 1 3 R 1 4 (5-186) ss HO (n-Cl2H25) HH (5-187) ss HO (n — CjjHaa) HH (5-188) ss HO (n — Cl8H37) HH (5-189) ss H Ο (π—〇2〇Η4ι) HH (5-190) ss HO (n — Ca4H4fl) HH (5-191) ss H 〇 ( Π — C 2 8 ^ 5 7 HH (5-192) ss HO (n - C 3 〇H g | ) HH (5-193) ss HO (n-CeFl3) HH (5-194) ss HO (n-C8F17) HH (5-195 ) ss H 〇(n—C12F25) HH (5-199) s S e HO ( n - Ce H ! 9 ) HH (5-200) s S e HO ( n - C8 H ! 7 ) HH (5-201 s S e H 〇( Π 一 C 1 2 H 2 5 ) HH (5-202) ss H -iO HH (5-203) ss HHH (5-204) ss HHH (5-205) ss HHH (5 -206) ss HHH &lt;5-207) ss HHH (5-208) ss H —n-CgHi7 HH (5-209) ss HHH (5-210) ss H π-〇12η25 HH &lt;5-2ll) Ss H n-CigH33 HH (5-212) ss H Π*〇4Ηβ &lt; Vc4H9 HH 73 324142 201245173

No. z 1 z 8 R 1 1 R12 R* 3 R14 (5-213) ss H You HH (5-214) ss H -!~&lt;〇KrvC 丨13 HH &lt;5-219) s S e HHH ( 5-220) s S θ HHH (5-221) s S e H ^〇-heart·HH (5-222) s S e HHH (5-223) ss HHH (5-224) ss H -hDTHb HH ( 5-225) ss H HJ HH (5-226) ss HS^f»-CeHi7 KX HH (5-227) ss HHH (5-228) ss H s n-C12H25 -Hi HH (5-229) ss H s^n-CeFi3 •Hi· HH 74 324142 201245173

No. z 1 z * R 1 1 R 1 2 R 1 3 R 1 4 (5-230) ss HHH (5-234) s S Θ H ^\Ji HH (5-235) s S e H -Κχ, 3 HH (5-236) s S e HS^/n-C12H25 -HJI HH (5-237) s SH °8H17 HH (5-238) s SH sister FFHH (5-239) s SH ^-^^- 〇ch3 HH (5-240) s SHHH (5-241) ss H -!-^^-〇&lt;«-〇3咐HH (5-242) ss HHH (5-243) ss H -l-^ ^-Ofn-Ce^a) HH (5-244) ss HHH 75 324142 201245173

No. ζ 1 z 2 R 1 1 R12 R 1 3 R 1 4 (5-245) ss HHH (5~24θ) ss H -i-^3~0(n'Cl2Ha) HH (5-247) ss H ' !&quot;^3~°(n'Cl^33) HH (5-248) ss H 0(n-CeH13) 〇(n-CeHi^ HH (5-249) ss HN==/ n-Crf=13 HH (5-253) s S e H -1h^^-och3 HH (5-254) s S θ H -|-&lt;^^-〇(n-C3H7) HH (5-255) s S e HHH (5-256) s SHHH (5-257) s SH heart. ',3 HH (5-258) ss HHH (5-259) ss H -hCT〇, CioH21 HH &lt;5-260) ss H heart. :_5 H H 76 324142 201245173

No. z 1 z * R 1 1 R12 R 1 3 R 1 4 (5-262) s S θ H -丨HH (5-263) S Θ s H -ι·\Τ〇'π'〇2〇Η41 HH (5-264) ss H 々. W17 HH (5-265) s S e H -H〇T〇, Cl4Ha HH (5-266) ss HHH (5-267) ss H -Si (CH 3) 2 ( n -Ca Ht T) HH (5 -268) ss H -Si (CH 3) 2 ( n - c10h21) HH (5-269) ss HHH (5-270) ss HHH (5-271) ss H 4~&lt;chz)«~^~^ HH (5-272) ss H -Η〇Η2) ι〇-〇&gt; HH (5-273) ss HHH (5-274) ss H X (CH 23⁄4 ~^^-n-CeH !3 HH (5 -275) ss HHH (5-276) ss HHH (5-278) s S e HHH (5-279) ss .H -hcHa)-^jl HH (5-280) s S e H -hcHik-^jl HH 77 324142 201245173

No. z 1 z 3 R 1 1 R12 R 1 3 R 1 4 &lt;5-281) ss HHH (5-282) ss H -hcH-heart HH (5-283) ss HHH (5-284) ss HHH ( 5-285) ss H -l-tCFde^jl HH (5-286) ss HHH (5-287) ss H -hcH2)8H(jQ HH (5-288) ss H -|-(CH2)e-^ Ji^-FHH (5-289) ss H - Bu (heart ^〇〇HH (5-290) S e S e H -Hch2)i2h^]QHH (5-291) ss H -hcn2&gt;,e"3 HH (5-292) ss H -Si (CH 3) 3 HH (5-293) ss H -S i (C*HS) 3 HH (5-294) ss H —Si ( i — C a H 7 ) 3 HH (5-295) ss H -Si (CH 3) 2 ( t -C * Η» ) HH (5-296) ss H -S i (CH3) 3 (n- C β H i 3 ) HH ( 5-297) ss H -Si (CH 3&gt; 2 ( n -C 1 2 H 2 8 ) HH 78 324142 201245173

No. z 1 z 2 R 1 1 R1 2 R 1 3 R 1 A (5-298) ss HH c h3 H (5-299) ss HH CaH5 H (5-300) ss HH n — 0 5 H j 3 H (5-301) ss HH rvCeH17 n-CgH^ H (5-302) ss HH n — C i 2 H 2 3 H (5-303) ss HH n—C33H&lt;5 H (5-304) ss HH n - C e F r 3 H (5-320) s S e HH c h3 H (5-321) s S e HH n - C 8 HL 7 H (5-323) S es HH n - C β H , a H (5-324) ss © HH n — C a ^ ir H (5-325) ss HH 〇c h3 H (5-326) ss HHO (n -C3Hr) H (5-327) ss HHO ( n - C eH , a ) H 79 324142 201245173

No. z 1 z 2 Rl 1 R 1 2 R 1 3 R 1 4 (5-328) ss HH 〇( n * C e F ia ) H (5-330) s S θ HHO (n- CeH13) H ( 5-331) ss HHH (5-332) ss HH -!hQ_CH3 H (5-333) ss HH -1-0-024, H (5-334) ss HH rvCeHn H (5-335) ss HHH (5 -336) ss HHH (5-339) s S e HHH (5-340) s S Θ HHH (5-341) ss HH -丨Ό H (5-342) ss HHS^n-CeHia -\&lt;s H (5-343) ss HH -HtrceFi3 H (5-344) ss HH -ktf H 80 324142 201245173 No. z 1 z 8 R1 1 Rl 2 R 1 3 R 1 4 (5-347) s S e HH -• A3 Η (5-348) s S e HH Η (5-349) ss HH Η (5-350) ss HH _^〇^ocH3 Η &lt;5-351) ss HH Η (5-352) ss HH Η (5-354) s S e HH -Ιη^^-ΟΙπ-Ο,οΗζ,) Η (5-355) ss HH Office. , ' Η (5-356) ss HH Η (5-357) s S θ HH Η (5-358) ss HH -ΚΧ0, · Η (5-359) s S e HH Η (5-360) s SHH - You Guang 17 Η (5-361) ss HH —S i (CHg) 2 (n. — C 1 〇Η 2 1 ) Η 81 324142 201245173

No. z 1 z * Rl 1 R1 a R 1 3 R14 (5-362) ss HH ~Hch2) - H (5-363) ss HHH (5-364) ss HHFFH (5-365) ss HHH (5-367 ) s S e .HHH (5-368) s SHH -Hch2)-^j| H (5-369) ss HH -Η〇Η2), η(Τ〇^ H (5-370) ss HH - Bu (4) *^0 r H (S-371) S e S e HH -hCH—O〇H (5-372) ss HH -Si (CH s) 3 H (5-373) ss HH -Si ( i - C 3 H 7) 3 H (5-374) ss HH -Si (C H3) z ( t - C *He) H 82 324142 201245173 No. z 1 z 2 Rl 1 Rl 2 R 1 3 R1 4 (5-375) ss HHH c h3 (5-376) ss HHH c2 Hs (5-377) ss HHH i-C3Hft (5-378) ss HHH n — C 4 H 9 (5-379) ss HHHN (5-380) ss HHH Π —C (JH 1 3 (5-381) ss HHH n.— Ci2H25 (5-382) ss HHH n—(5-383) ss HHH n* — Ci9H39 (5-384) ss HHH n - C e F j 9 (5-385) ss HHH n - C i 2 F 2 5 (5-393) s S e HHH c h3 (5-394) s S e HHH n — C $ H i 3 (5-396) S es HHH n — C β H ia (5-397) SS e HHH n. ** C g F 17 (5-398) SSHHH OC2H5 (5-399) S s HHHO (n- CeHia) (5-400) ss HHHO( π — C i 〇 H 2 i) 83 324142 201245173

No. z 1 z * R 1 1 Rl e R 1 3 R 1 4 &lt;5-401) ss HHHO ( n- C e F t 3) (5-403) s S e HHHO (neC8Hir) (5-404 ) ss HHH &lt;5-405) ss HHH -!〇-ch3 (5-406) ss HHH -!〇-^ (5-407) ss HHH (5-409) s S e HHH -IO (5-410 ) ss HHH (5-41L) ss HHH -KT-7 (5-412) ss HHH -HDTeF13 (5-413) ss HHH -i\TF (5-415) s S e HHH (5-416) ss HHH -H^^-〇ch3 (5-417) ss HHH 84 324142 201245173 No. z 1 z 2 Rl 1 R12 R 1 3 R 1 4 (5-418) ss HHH (5-420) s S e HHH -!Η ^-〇(η-〇3Η7) {5-421) ss HHH -Kj. ,, 13 {5-423) s S e H H H -ΚΤ〇, η·°^3 (5-424) S Θ s H H H • KJ〇, n_C2〇H41 (5-425) s s H H H Heart. W17 (5-426) ss HHH + (called -〇(5-427) ss HHH (5-428) ss HHH (5-429) S Θ S e HHH -I-(ch2)12-^]Q (5 -430) ss HHH -Si (CH3) 3 (5-431) ss HHH -S i (C2H5) 3 (5-432) ss HHH —Si ( i — C 3 H 7 ) 3 (5-433) ss HHH -Si (CH3) * ( t -C 4 He)

No. R 1 z 1 z 2 R&quot; R 12 R13 R 14 &lt;5-434) ch3 ss CHS C Hs ch3 H (5-435) ch3 ss c2H3 c2hb C 2 H 3 H (5-436) ch3 ss n- CsHr n ~C3Hr Π _ C 3 H 7 H (5-437) CHa ssn — C β H 13 n — C 9 H i 3 n C β H ia H &lt;5-438) CHg ssn ~ c ! 2 H 2 5 n—C12H2B n — C i 2 H 2 3 H (5-439) CH3 ss C Ha n — C!2H25 CHg H {5-440) CHa ss HC Hg ch3 H (5-441) ch3 ss H n - C β H ian - C β H ! g H (5-442) ch3 ss 〇ch3 OC Ha 〇ch3 H (5-443) ch3 ss O (nC 3 H r) O ( n - C 3 H r) O ( n - C 3 H r) H (5-444) CHa ss oc h3 H oc h3 H (5-445) ch3 ss och3 n - C β H ia oc h3 H 85 324142 201245173 The wavy line of Table 3 refers to the bond .

(W52) Specific examples of the preferred fused polycyclic compound (5) containing an oxygen group element, for example, numbers (5-1), (5-2), (5-3), (5-5), (5_6) , (5-8), (5-10), (5-35), (5-37), (5-41), (5-42), (5-49), (5-51), ( 5-52), (5-56), (5-57), (5-58), (5-68), (5-73), (5-81), (5-82), (5- 83), (5-84), (5-85), (5-86), (5-87), (5-88), (5-89), (5-90), (5-91) , (5-93), (5-94), (5-95), (5-96), (5-98), (5-101), (5-103), (5-107), ( 5-108), (5-110), (5-112), (5-113), (5-114), (5-177), (5-178), (5-181), (5- 184), (5-186), (5-202), (5-203), (5-207), (5-212), (5-213), (5-223), (5-225) , (5-228), (5-230), (5-239), (5-243), (5-246), (5-248), (5-257), (5-260), ( 5-269), (5-271), (5-279), (5-291), (5-298), (5-299), (5-300), (5-302), (5- 325), (5-327), (5-331), (5-332), (5-334), (5-341), (5-344), (5-350), (5-362) , 5-375), (5'376), (5-380), (5-381), (5-398), (5-399), (5-404), (5-410) and (5- 416) shown. 324142 86 201245173 * More examples are number (5-1), (5-2), (5-5), (5-6), (5-35), # (5-37), (5-81) ), (5-82), (5-83), (5-84), (5-85), (5-86), - (5_87), (5-89), (5-90), ( 5-93) , (5-96), (5-98), , (5_103), (5-112), (5-1Π), (5-178), (5-181), (5-184) ), (5_202), (5-203), (5-207), (5-223), (5-225), (5-230), (5_239), (5-298), (5-299) ), (5-300), (5-302), (5-325), (5_327), (5-331), (5-332), (5-375), (5-376), (5 -380), (5-381) and (5_399). EXAMPLES Hereinafter, the present invention will be specifically described by way of examples. Synthesis of <2,5-dibromo-3,4-dimethyl sulfinyl porphin 1) 1) NBS, dioxane 2) H20 I \ 3) NBS 〇=SS=0 4) Na2C03 aq , \__/ &quot; Br- d \ at room temperature, in 3, 4-dimethylsulfonylthiophene (2.50 g, 14. 2 mmol) of dioxane (267 ml) The solution was added with N-bromosuccinimide (3·85 S, 21.6 mmol) and stirred for 6 hours. Then, N-Moglass oxime imine (0.96 g, 5.39 mmol) was added and stirred for 2 hours. To the reaction mixture, water (115 ml) and N-bromosuccinimide (3. 85 g, 21.6 mmol) were added, and the mixture was stirred at the same temperature for 2 hours. Then, N-bromosuccinimide (3·85 g, 21. 6 Torr) was further added, and the mixture was stirred for 4 hours and 30 minutes. After the reaction was completed, the reaction mixture was evaporated. The mixture was washed with water and a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The obtained crude product was purified by a silica gel column (developing solvent·methanol-ethyl acetate) to obtain 2,5-dibromo-3,4-dimethyl-decylthiophene· 73 g. (yield μ%) ^-NMRCCDCh ^ 6ppm): 3.21 (s, 2.4H), 3.09 (s, 3.6H) Synthesis of <2, 5-dibromo-3, 4-didecylsulfinylthiophene 2>

To a solution of 3, 4-methyl-methyl ketone (83 mg, 0.47 mmol) in Ershiyuan (11.6 ml) and water (5.0 ml), add N - Bromoammonium imine (336 mg, 1.89 mmol), stirred for 4 hours and 40 minutes. Then, N-bromosuccinimide (168 mg, 0.95 mmol) was added and stirred for 2 hours. A portion of the reaction solution was taken and treated with a saturated aqueous solution of sodium carbonate. Formation of 2,5-dibromo-3,4-didecyl sulphate. <2, 5-bis(4-n-hexylphenyl)-3,4-diindenylsulfinyl (combination of thiophene)

PdCiydppf) CS2CO3 Dissolve 2, 5-dibromo-3, 4-didecyl sub-organisms (〇.g, 〇. 2 324142 88 201245173 • millimolar) in 9 ml of THF and dissolve in the obtained Liquid, adding 4_n-hexyl + (4' 4' 5' 5-tetradecyl-1,3, 2-dioxaborane-2-yl) stupid (〇. 17g, 0.6 millimolar) and carbonic acid planing Aqueous solution (2. 〇Μ, 2.9 ml). To make up the money in the silk room, add cis 2 (dppf) (〇· 〇9 g, 0.01 mmol), then warm to 8 generations, and stir for 6 hours. After the resulting reaction solution was cooled to room temperature, an aqueous gasification solution was added to separate the organic layer and the aqueous layer. The aqueous layer was extracted with THF and mixed with an organic layer. The mixed organic layer was washed with water and a saturated aqueous solution of sodium chloride, then dried over sodium sulfate and concentrated to give a crude product. The obtained crude product was separately obtained by using thin layer chromatography to obtain 25-bis(4'-n-hexylphenyl)-3,4-dimethylsulfinylthiophene having the following spectrum. lH-NMR (CDCl3 ^ 5ppm): 7. 45 (d, J = 8. 1 Hz, 2. 5H), 7. 36 (d J = 8. 1 Hz, 1.5H), 7.28-7.24 (m, 4H), 3.28 (s, 2 3H) 3. 09(s,3.7H)' 2.70-2.63 (m,4H), 1.7 (M.53(m,4H), 1.42-1.28 (m, 12H), 0.92-0.87 ( m, 6H) Synthesis of bis(5-hexylbenzo[4,5]thieno)[3,2-c: 2,,3, —e]thiophene

CeHta 1) CF3S〇3H.P205 2) it*

2,5-bis(4,-n-hexylphenyl)-3,4-dimethyl acryl porphin (0·30 g, 0.6 mmol) and p2〇5 (〇. 〇 3 g, 〇· 2 mmoles, and solution of 10·3 ml of trifluoromethanesulfonic acid to obtain a reaction liquid. The solution was heated to 50 ° C, stirred at the same temperature for 3 hours, and then cooled to room temperature = 324142 89 201245173 to the reaction liquid. The reaction solution was added to 103 ml of water, and the precipitated solid was filtered. The obtained solid was washed with water and then dissolved in hydrazine (9 liters of pyridine), and the resulting solution was heated and stirred under reflux for 10 hours. The solution was cooled to room temperature, and water and trioxane were added. The obtained organic layer and aqueous layer were separated, and the organic layer was dried with sulfuric acid and concentrated to give a crude product. The obtained crude product was purified by using a silica gel column and gel permeation chromatography to obtain bis(5-hexylbenzo[4,5]nonphene)[3,2-c: 2,,3,-e&gt; 'H-NMRCCDCh ' 6ppm): 7.65 (d, J=7. 3Hz, 2H), 7 57 J'l.OHz, 2H), 7.19 (dd, J=7.3, 1.0Hz, 2H) 2 73 (t J =7.0 Hz, 4H), 1.73-1.63 (m, 4H), 1.4 (M.29 (m, 12H)' 0.90 (t, J = 6.8 Hz, 6H) ' ' Industrial utilization possibility by the present invention The manufacturing method can be used in a mild condition, and there are condensed multi-layered characters for oxygen-containing elements such as organic semiconductor materials. [Simple description] ° No [Main component symbol description] No 324142 90

Claims (1)

201245173 VII. Patent Application Range: 1. A method for producing a condensed polycyclic compound (5) containing an oxygen group element, comprising: an aromatic heterocyclic compound (1 a) represented by the formula (la) and an N-halogen Rebel amine, reacted in the presence of water or alcohol to give formula (2a) a step of the aromatic heterocyclic compound (2a) shown; an aromatic heterocyclic compound (2a) and a formula (3) The aromatic compound (3) shown is reacted to obtain the formula (4) R1 R1 n=21 71:0 D11 a step of the compound (4) shown; and reacting the compound (4) with an acid to obtain the formula (5) 324142 1 4 4201245173 The step of condensed polycyclic compound (5) containing an oxygen group element; i, wherein R, which represents a carbon number of 1 to 20, independently represent: atom 3 or selenium? Z2 represents an oxygen atom, a sulfur atom or a selenium atom, and τ, 尺 and R are independently represented by a hydrogen atom, and a carbon atom of 1 to 30 which can be substituted, and a carbon number of 1 to 30 which can be substituted The base may be obtained by an aromatic group having 6 to 3 carbon atoms, an alkyl group having 7 to 30 carbon atoms which may be substituted, a heteroaromatic group having 4 to 3 carbon atoms which may be substituted, and may be substituted. a substituted aramid wire having a carbon number of 5 to 3 G or a substituted tartan group represented by the formula 2) 3 (R independently represents a carbon number which may be substituted) to a calcined group of 3 Å or a carbon number which may be substituted 6 To the aromatic group of 3〇); χ1 represents a tooth atom, and X2 represents a leaving group). 2. The method of claim 2, wherein any of ζ, and ^ is a sulfur atom. 3. The method of claim 1, wherein the ν-dentate slow-melting amine is Ν-halogen amber quinone. A method for producing an aromatic heterocyclic compound (5), which comprises: an aromatic heterocyclic compound (5) represented by the formula (la) ζί V ^ (1a) and a (tetra) ugly amine in water 324142 2 201245173 or an alcohol React in the presence of the formula to obtain the formula (2a) a step of the aromatic heterocyclic compound (2a) shown; (in the formula, 'R1 represents an alkyl group having a carbon number of ii 2 吖, respectively, represents an ==) atom, and z2 represents an oxygen atom, a sulfur atom or an atom; 5. Any of the methods H described in claim 4 of the patent application is a sulfur atom. And Z. 6. The method of claim 4, wherein the amine is N-halogen peryleneimine. A few halogens 324142 201245173 * Fourth, the designated representative map: - (a) the representative representative of the case is: () map. (There is no picture in this case) (2) A brief description of the symbol of the representative figure: (none) 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 324142 5