JP2005281243A5 - - Google Patents

Claims (27)

Formula (1):

(In the formula, n is an integer of 1 to 8, X is a halogen, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents are a halogen or an aromatic ring. A trihalosilyloligothiophene compound which may be substituted with In the formula (1),
In the formula, n is an integer of 1 to 8, X is a halogen, R ¹ is H, C _1-20 alkyl, or an aromatic ring, and these substituents are substituted with a halogen or an aromatic ring. The trihalosilyl oligothiophene compound according to claim 1 , wherein R ² is H. In the formula (1),
In the formula, n is an integer of 1 to 8, X is a halogen, R ¹ is H, C _1-20 alkyl, or an aromatic ring, and these substituents are substituted with a halogen or an aromatic ring. The trihalosilyl oligothiophene compound according to claim 1 , wherein R ² is C _1-20 alkyl. In the formula (1),
Wherein, n is an integer of 1 ~ 8, X is halogen, and R ¹ is substituted with a halogen or an aromatic ring is C _1-20 alkyl but it may also, according to claim R ² is H 1. The trihalosilyl oligothiophene compound according to 1. In the formula (1),
The trihalosilyl oligothiophene compound according to claim 1, wherein n is an integer of 1 to 8, X is halogen, and R ¹ and R ² are H. In the formula (1),
Wherein, n is an integer of 1 ~ 8, X is a halogen, a C _1-7 alkyl R ¹ is not good may be substituted by halogen or an aromatic ring, according to claim R ² is at H 1. The trihalosilyl oligothiophene compound according to 1. In the formula (1),
Wherein, n is an integer of 1 ~ 8, X is halogen, and R ¹ is substituted with a halogen or an aromatic ring is C _8-20 alkyl but it may also, according to claim R ² is H 1. The trihalosilyl oligothiophene compound according to 1. Formula (2):

(In the formula, n is an integer of 1 to 8, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents may be substituted with a halogen or an aromatic ring. well, R ³ is a trialkoxysilyl oligothiophene compound represented by C _1-4 Ru alkyl der). In the formula (2),
In the formula, n is an integer of 1 to 8, R ¹ is H, C _1-20 alkyl, or an aromatic ring, and these substituents may be substituted with a halogen or an aromatic ring, and R ² is 9. The trialkoxysilyl oligothiophene compound according to claim 8, wherein the compound is H and R ³ is C _1-4 alkyl. In the formula (2),
In the formula, n is an integer of 1 to 8, R ¹ is H, C _1-20 alkyl, or an aromatic ring, and these substituents may be substituted with a halogen or an aromatic ring, and R ² is The trialkoxysilyl oligothiophene compound according to claim 8, wherein the compound is C _1-20 alkyl and R ³ is C _1-4 alkyl. In the formula (2),
Wherein, n is an integer of 1 ~ 8, R ¹ is H, or halogen, C _1-20 alkyl but it may also be substituted with an aromatic ring, R ² is H, R ³ is C _4alkyl der Ru請 Motomeko 8 trialkoxysilyl oligothiophene compound according. In the formula (2),
The trialkoxysilyl oligothiophene compound according to claim 8, wherein n is an integer of 1 to 8, R ¹ and R ² are H, and R ³ is C _1-4 alkyl. In the formula (2),
Wherein, n is an integer from 1 to 8, a C _1-7 alkyl R ¹ is not good may be substituted by halogen or an aromatic ring, R ² is H, R ³ is C _1-4 The trialkoxysilyl oligothiophene compound according to claim 8, which is alkyl. In the formula (2),
Wherein, n is an integer of 1-8, and R ¹ is substituted with a halogen or an aromatic ring is C _8-20 alkyl but it may also, R ² is H, R ³ is C _1-4 The trialkoxysilyl oligothiophene compound according to claim 8, which is alkyl. Formula (3):

(In the formula, n is an integer of 1 to 8, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents may be substituted with a halogen or an aromatic ring. and oligothiophene compound represented by good), the oligothiophene metal compound obtained by metallation reaction by reacting an organometallic compound, reacted tetrahalosilane compound (SiX _4), equation (1):

(In the formula, n is an integer of 1 to 8, X is a halogen, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents are a halogen or an aromatic ring. A trihalosilyl oligothiophene compound represented by (optionally substituted ) , and then reacting the trihalosilyl oligothiophene compound with alcohol (R ³ OH) in the presence of a base, Formula (2)

(In the formula, n is an integer of 1 to 8, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents may be substituted with a halogen or an aromatic ring. well, R ³ is a manufacturing method of trialkoxysilyl oligothiophene compound represented by C _1-4 Ru alkyl der).   The trialkoxysilyl according to claim 15, wherein the organometallic compound is an organolithium compound, and the solvent used is an ether-based, aromatic-based, aliphatic hydrocarbon-based solvent, or a mixture thereof. A method for producing an oligothiophene compound. The method for producing a trialkoxysilyl oligothiophene compound according to claim 15, wherein 2 to 50 moles of tetrahalosilane compound (SiX ₄ ) are reacted with 1 mole of oligothiophene metal compound. Formula (3):

(In the formula, n is an integer of 1 to 8, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents may be substituted with a halogen or an aromatic ring. The oligothiophene compound represented by ( good) and an organometallic compound are reacted with the oligothiophene metal compound obtained by the metalation reaction with a tetrahalosilane compound (SiX ₄ ). 1):

(In the formula, n is an integer of 1 to 8, X is a halogen, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents are a halogen or an aromatic ring. And may be substituted with a trihalosilyloligothiophene compound.   The trihalosilyl oligo according to claim 18, wherein the organometallic compound is an organolithium compound, and the solvent used is an ether-based, aromatic-based, aliphatic hydrocarbon-based solvent, or a mixture thereof. A method for producing a thiophene compound. The method for producing a trihalosilyl oligothiophene compound according to claim 18, wherein 2 to 50 moles of a tetrahalosilane compound (SiX ₄ ) are reacted with 1 mole of the oligothiophene metal compound. Formula (1):

(In the formula, n is an integer of 1 to 8, X is a halogen, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents are a halogen or an aromatic ring. in a tri-halo silyl oligothiophene compound represented by it may be substituted) and the alcohol (R ³ OH), characterized in that to the presence of a base reaction, equation (2):

(In the formula, n is an integer of 1 to 8, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents may be substituted with a halogen or an aromatic ring. well, R ³ is a manufacturing method of trialkoxysilyl oligothiophene compound represented by C _1-4 Ru alkyl der). Formula (4):

(In the formula, n is an integer of 1 to 8, Y is a halogen, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents are a halogen or an aromatic ring. The oligothiophene metal compound obtained by the halogen-metal exchange reaction by reacting the oligothiophene halogen compound represented by (1 ) with an organometallic compound, or an alkali metal or an alkaline earth metal, Formula (1) obtained by reacting a halosilane compound (SiX ₄ ):

(In the formula, n is an integer of 1 to 8, X is a halogen, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents are a halogen or an aromatic ring. (May be replaced with )
Wherein the trihalosilyloligothiophene compound represented by the formula (2) is reacted with an alcohol (R ³ OH) in the presence of a base:

(In the formula, n is an integer of 1 to 8, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents may be substituted with a halogen or an aromatic ring. well, R ³ is a manufacturing method of trialkoxysilyl oligothiophene compound represented by C _1-4 Ru alkyl der). 23. The trialkoxy according to claim 22, wherein the organometallic compound is an organolithium compound, and the solvent used is an ether, aromatic, aliphatic hydrocarbon solvent, or a mixture thereof. A method for producing a silyl oligothiophene compound. The method for producing a trialkoxysilyl oligothiophene compound according to claim 22, wherein 2 to 50 mol of tetrahalosilane compound (SiX ₄ ) is reacted with 1 mol of the oligothiophene metal compound. Formula (4):

(In the formula, n is an integer of 1 to 8, Y is a halogen, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents are a halogen or an aromatic ring. The oligothiophene metal compound obtained by the halogen-metal exchange reaction by reacting the oligothiophene halogen compound represented by (1 ) with an organometallic compound, or an alkali metal or an alkaline earth metal, Formula (1), characterized by reacting a halosilane compound (SiX ₄ ):

(In the formula, n is an integer of 1 to 8, X is a halogen, R ¹ and R ² are each H, C _1-20 alkyl, or an aromatic ring, and these substituents are a halogen or an aromatic ring. (May be replaced with )
The manufacturing method of the trihalosilyl oligo thiophene compound shown by these. The trihalosilyl group according to claim 25, wherein the organometallic compound is an organolithium compound, and the solvent used is an ether-based, aromatic-based, aliphatic hydrocarbon-based solvent, or a mixture thereof. A method for producing an oligothiophene compound. The method for producing a trihalosilyl oligothiophene compound according to claim 25, wherein 2 to 50 mol of tetrahalosilane compound (SiX ₄ ) is reacted with 1 mol of oligothiophene metal compound.