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Chalcogen-containing fused-ring polycyclic organic material and process for producing the same

Foreign code F110004862
File No. K05607WO
Posted date Jul 22, 2011
Country Republic of Korea
Application number 20067021054
Gazette No. 20060117379
Gazette No. 100835427
Date of filing Oct 10, 2006
Gazette Date Nov 16, 2006
Gazette Date Jun 9, 2008
International application number JP2005004006
International publication number WO2005087780
Date of international filing Oct 10, 2006
Date of international publication Sep 22, 2005
Priority data
  • P2004-068039 (Mar 10, 2004) JP
Title Chalcogen-containing fused-ring polycyclic organic material and process for producing the same
Abstract A diacetylene derivative is used as a starting material and subjected to dilithiation with an organolithium compound reagent.
The resultant reaction product is reacted with an excess chalcogen (sulfur or selenium), whereby intramolecular cyclization proceeds and, simultaneously therewith, the skeletons of three rings are formed.
A chalcogen- containing fused-ring polycyclic organic material having a dichalcogenide bond was found to be thus obtained.
It was also found that by subjecting the resultant compound to a chalcogen elimination reaction, a heteroacene is obtained in a satisfactory yield.
These synthesis techniques have made it possible to synthesize a series of highly planar chalcogen-containing pi-electron system materials.
Thus, a chalcogen-containing fused- ring polycyclic organic material having excellent charge-transporting properties and a process for producing the material can be provided.
Scope of claims [claim1]

[1] the following expression (1)

[Of 21]

(1)


(The shows E1 S or Se, Ar, benzene, substituted benzene, naphthalene, replace enough Talen, anthracene, replace anthracene, h. age of fen, replacement check out age of fen, francs, substituted furan, pyrrole, substituted pyrroles, selenophene, replace selenophene, pyridine, replace pridi, thiazole, substituted thiazole, bennzochiofenn, replace bennzochiofenn, benzo furan, replace mildew on ZOFRAN, indole, or put ^ double binding site of one of the NDR Shows through, and cyclopropane, E ^ except when S Ar = benzene), including-cyclopropane structure indicated that characterized many polycyclic organic material.



(Type in the
R2, R3and R4 the heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, monovalent substituted heterocycle, monovalent oligo heterocyclic ring based, monovalent substituents oligosaccharide complex environment on, hydrogen atom, alkyl, alkoxy, arquilti o based, ariiruokishi based, ariiruchio based, ariiruarukiru, ariiruaruコkishi based, ariiruarukiruchio based, aruke - Le based, substituents arc - Le, Archi - Le based, substituents archi - Le, ariru based, amino, amino substituents, azo based, carboxyl, Ashiru based, alkoxicarbo - Le based, formyl, Nitro, shiano based, Cyril based, silyl substituents, Stan - Le base, substituents Stan - Le, boril of Bulgaria based, substituents boril of Bulgaria, Hoshino based, substituents ho Shin, shiriruokishi based, shiriruokishi substituents, ariirusurufo - ruokishi,! lucilsulfo - ruokishi based on the or halogen atoms indicates) in structure indicated having claim to feature section One of the listed contained-cyclopropane many polycyclic organic material.

The following expression (3)

[Of 23]



(Type in the
R2, R3and R4and R5, R6, R7, R8 the heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, monovalent substituted heterocycle, oligosaccharide heterocycle 1, monovalent substituents oligosaccharide complex environment on, hydrogen atom, alkyl, alcoi system based, alkylthio, ariiruoisi, Ariiruchio based, ariiruarukiru based,? c? c reelalkoxi based, ariiruarukiruchio, aruke - Le base, substituents aruke - Le, archi - Le base, substituents alkynyl, ariru based, amino, amino substituents, azo based, Calvo ethylhexyl, Ashiru based, alkoxicarbo - Le based, formyl, Nitro, shiano based, Siri Le, silyl substituents, Stan - Le, replacing Stan - Le based, boril of Bulgaria based, substituents boril of Bulgaria, Hoth fin base, substituents Hoshino, shiriruokishi based, shiriruokishi substituents, ariirusurufo

-Ruokishi, alkylsulfo - ruokishi, or halogen atoms indicates the E1 = , S when! ^ = 1 ^ = 1 ^3= 1 ^ = 1 ^ = 1 ^ = 1 ^ = 1 ^ unless a = hydrogen atoms), including-cyclopropane of claim 1 having the structure indicated that characterized many polycyclic organic material. The following formula (4)

[Of 24]



(The R R2, R3and R4and R6, R7, is a heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, monovalent substituted heterocycle, oligosaccharide heterocycle 1, monovalent substituents oligosaccharide complex environment on, hydrogen atom, alkyl, alcoi system based, alkylthio groups, ariiruoisi, ariirucio, ariiruaruiru based, it Reelalkoxi, ariiruarukiruchio based, aruke - Le based substituent aruke - Le, archi - Le based, Carmenza substituents, ariru based, amino, amino substituents, azo based, Calvo ethylhexyl based, Ashiru based, alkoxicarbo - Le based, formyl, Nitro, shiano based, Siri Le based, silyl substituents, Stan - Le, replacing Stan - Le base, boril of Bulgaria, substituents boril of Bulgaria, Hoth Fino, Hoshino substituents, shiriruokishi based, shiriruokishi substituents, ariirusurufo - ruokishi, Show alkylsulfo - ruokishi base, or halogen atoms), including-cyclopropane of claim 1, having the structure indicated that characterized many polycyclic organic material. As indicated by the following equation (5)

[Of 25]




(The X is that I, Br, or C1), diacetylene, whereas molecules in the triple ring of in reaction by claim 1, containing chalcogenide cyclopropane in many including CAL polycyclic organic material to get to pingdingbu cyclopropane many polycyclic organic material for making.

The metal halide Exchange reaction using organic metal bases, [6] wherein diacetylene, containing chalcogenide cyclopropane of claim 5 features to react-unit E1 and through jimeta rich that after the many polycyclic organic material manufacturing method.

[7] the following expression (9)

[Of 26]



(The E indicates S or Se, Ar, benzene, substituted benzene, naphthalene, replace enough Talen, anthracene, replace anthracene, h. age of fen, replacement check out age of fen, francs, substituted furan, pyrrole, substituted pyrroles, selenophene, replace selenophene, pyridine, replace pridi, thiazole, substituted thiazole, bennzochiofenn, replace bennzochiofenn, benzo furan, replace mildew on ZOFRAN, indole, or put ^ shows through double binding site of one of the NDR cyclopropane units, E Except when 1 = S Ar = benzene) in designated to include-cyclopropane compounds in te roascensi must be characterized to many polycyclic organic material.

The following expression (10)

[Of 27]



(The R R2, R3and R4 the heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, one substituted heterocycle, oligosaccharide HETEROCYCLES with monovalent, monovalent substituents oligosaccharide complex ring on, hydrogen atom, alkyl, alkoxy, arquilti o based, ariiruokishi based, ariiruchio based, ariiruarukiru based, ariiruarukokishi based, ariiruarukiruchio based, aruke - Le based on the Substituent arc - Le, archi - Le base, substituents archi - Le, ariru based, amino, amino substituents, azo based, carboxyl, Ashiru based, alkoxicarbo - Le, formyl, Nitro, shiano based, Cyril based, silyl substituents, Stan - Le based, replacing Stan - Le base, boril of Bulgaria, substituents boril of Bulgaria, Hoshino, Ho Shin substituents, shiriruokishi based, substituted shiriruokishi, ariirusurufo - ruokishi based on the? c? c lucilsulfo-ruokishi base, or halogen atoms shows E1 = When the S 1 ^ = 1 ^ = 1 ^ except in hydrogen atoms =4R = hydrogen atoms, or = methyl and R2= R3R 4= ) in having the structure indicated of claim 7 to feature that the compounds in the heteroasenni must contain chalcogen cyclopropane many polycyclic organic material.

[9] the following expression (11)

[Of 28]


(The R R2, R3and R4and R5, R6, R7, R8 the heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, monovalent substituted heterocycle, oligosaccharide heterocycle 1, monovalent substituents oligosaccharide complex environment on, hydrogen atom, alkyl, alcoi system based, alkylthio, ariiruokishi The ariiruchio based, ariiruarukiru based,? c? c reelalkoxi based, ariiruarukiruchio, aruke - Le base, substituents aruke - Le, archi - Le base, substituents alkynyl, ariru based, amino, amino substituents, azo based, Calvo ethylhexyl, Ashiru based, alkoxicarbo - Le based, formyl, Nitro, shiano based, Siri Le, silyl substituents, Stan - Le, replacing Stan - Le based, boril of Bulgaria based, substituents boril of Bulgaria, Hoth fin base, substituents Hoshino, shiriruokishi based, shiriruokishi substituents, ariirusurufo

-Shows ruoisi, alkylsulfo - ruoisi, or halogen atoms, E1 = S when the 1 ^ = 1 ^ = 1 ^ = 1 ^ = 1 ^ = 1 ^ = 1 ^ = 1 ^ unless a = hydrogen atoms) in having the structure indicated of claim 7 to feature that the compounds in the eteroasenni must include CAL CoGe, cyclopropane many polycyclic organic material.

The following expression (12)

[Of 29]


(Type in the
R2, R3and R4and R5, R6, R7, R8 the heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, monovalent substituted heterocycle, oligosaccharide heterocycle 1, monovalent substituents oligosaccharide complex environment on, hydrogen atom, alkyl, alcoi system based, alkylthio, ariiruokishi, Ariiruchio based, ariiruarukiru based,? c? c reelalkoxi based, ariiruarukiruchio, aruke - Le base, substituents aruke - Le, archi - Le base, substituents alkynyl, ariru based, amino, amino substituents, azo based, Calvo ethylhexyl, Ashiru based, alkoxicarbo - Le based, formyl, Nitro, shiano based, Siri Le, silyl substituents, Stan - Le, replacing Stan - Le base, boril of Bulgaria, substituents boril of Bulgaria, Hoth Fino, Hoshino substituents, shiriruokishi based, shiriruokishi substituents, ariirusurufo - Show ruokishi, alkylsulfo - ruokishi, or halogen atoms) in indicated, having a structure of claim 7 to feature that the compounds in the heteroasenni must include, Gen cyclopropane many polycyclic organic material.[1] the following expression (1)

[Of 21]

(1)


(The shows E1 S or Se, Ar, benzene, substituted benzene, naphthalene, replace enough Talen, anthracene, replace anthracene, h. age of fen, replacement check out age of fen, francs, substituted furan, pyrrole, substituted pyrroles, selenophene, replace selenophene, pyridine, replace pridi, thiazole, substituted thiazole, bennzochiofenn, replace bennzochiofenn, benzo furan, replace mildew on ZOFRAN, indole, or put ^ double binding site of one of the NDR Shows through, and cyclopropane, E ^ except when S Ar = benzene), including-cyclopropane structure indicated that characterized many polycyclic organic material.



(Type in the
R2, R3and R4 the heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, monovalent substituted heterocycle, monovalent oligo heterocyclic ring based, monovalent substituents oligosaccharide complex environment on, hydrogen atom, alkyl, alkoxy, arquilti o based, ariiruokishi based, ariiruchio based, ariiruarukiru, ariiruaruコkishi based, ariiruarukiruchio based, aruke - Le based, substituents arc - Le, Archi - Le based, substituents archi - Le, ariru based, amino, amino substituents, azo based, carboxyl, Ashiru based, alkoxicarbo - Le based, formyl, Nitro, shiano based, Cyril based, silyl substituents, Stan - Le base, substituents Stan - Le, boril of Bulgaria based, substituents boril of Bulgaria, Hoshino based, substituents ho Shin, shiriruokishi based, shiriruokishi substituents, ariirusurufo - ruokishi,! lucilsulfo - ruokishi based on the or halogen atoms indicates) in structure indicated having claim to feature section One of the listed contained-cyclopropane many polycyclic organic material.

The following expression (3)

[Of 23]



(Type in the
R2, R3and R4and R5, R6, R7, R8 the heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, monovalent substituted heterocycle, oligosaccharide heterocycle 1, monovalent substituents oligosaccharide complex environment on, hydrogen atom, alkyl, alcoi system based, alkylthio, ariiruoisi, Ariiruchio based, ariiruarukiru based,? c? c reelalkoxi based, ariiruarukiruchio, aruke - Le base, substituents aruke - Le, archi - Le base, substituents alkynyl, ariru based, amino, amino substituents, azo based, Calvo ethylhexyl, Ashiru based, alkoxicarbo - Le based, formyl, Nitro, shiano based, Siri Le, silyl substituents, Stan - Le, replacing Stan - Le based, boril of Bulgaria based, substituents boril of Bulgaria, Hoth fin base, substituents Hoshino, shiriruokishi based, shiriruokishi substituents, ariirusurufo

-Ruokishi, alkylsulfo - ruokishi, or halogen atoms indicates the E1 = , S when! ^ = 1 ^ = 1 ^3= 1 ^ = 1 ^ = 1 ^ = 1 ^ = 1 ^ unless a = hydrogen atoms), including-cyclopropane of claim 1 having the structure indicated that characterized many polycyclic organic material. The following formula (4)

[Of 24]



(The R R2, R3and R4and R6, R7, is a heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, monovalent substituted heterocycle, oligosaccharide heterocycle 1, monovalent substituents oligosaccharide complex environment on, hydrogen atom, alkyl, alcoi system based, alkylthio groups, ariiruoisi, ariirucio, ariiruaruiru based, it Reelalkoxi, ariiruarukiruchio based, aruke - Le based substituent aruke - Le, archi - Le based, Carmenza substituents, ariru based, amino, amino substituents, azo based, Calvo ethylhexyl based, Ashiru based, alkoxicarbo - Le based, formyl, Nitro, shiano based, Siri Le based, silyl substituents, Stan - Le, replacing Stan - Le base, boril of Bulgaria, substituents boril of Bulgaria, Hoth Fino, Hoshino substituents, shiriruokishi based, shiriruokishi substituents, ariirusurufo - ruokishi, Show alkylsulfo - ruokishi base, or halogen atoms), including-cyclopropane of claim 1, having the structure indicated that characterized many polycyclic organic material. As indicated by the following equation (5)

[Of 25]




(The X is that I, Br, or C1), diacetylene, whereas molecules in the triple ring of in reaction by claim 1, containing chalcogenide cyclopropane in many including CAL polycyclic organic material to get to pingdingbu cyclopropane many polycyclic organic material for making.

The metal halide Exchange reaction using organic metal bases, [6] wherein diacetylene, containing chalcogenide cyclopropane of claim 5 features to react-unit E1 and through jimeta rich that after the many polycyclic organic material manufacturing method.

[7] the following expression (9)

[Of 26]



(The E indicates S or Se, Ar, benzene, substituted benzene, naphthalene, replace enough Talen, anthracene, replace anthracene, h. age of fen, replacement check out age of fen, francs, substituted furan, pyrrole, substituted pyrroles, selenophene, replace selenophene, pyridine, replace pridi, thiazole, substituted thiazole, bennzochiofenn, replace bennzochiofenn, benzo furan, replace mildew on ZOFRAN, indole, or put ^ shows through double binding site of one of the NDR cyclopropane units, E Except when 1 = S Ar = benzene) in designated to include-cyclopropane compounds in te roascensi must be characterized to many polycyclic organic material.

The following expression (10)

[Of 27]



(The R R2, R3and R4 the heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, one substituted heterocycle, oligosaccharide HETEROCYCLES with monovalent, monovalent substituents oligosaccharide complex ring on, hydrogen atom, alkyl, alkoxy, arquilti o based, ariiruokishi based, ariiruchio based, ariiruarukiru based, ariiruarukokishi based, ariiruarukiruchio based, aruke - Le based on the Substituent arc - Le, archi - Le base, substituents archi - Le, ariru based, amino, amino substituents, azo based, carboxyl, Ashiru based, alkoxicarbo - Le, formyl, Nitro, shiano based, Cyril based, silyl substituents, Stan - Le based, replacing Stan - Le base, boril of Bulgaria, substituents boril of Bulgaria, Hoshino, Ho Shin substituents, shiriruokishi based, substituted shiriruokishi, ariirusurufo - ruokishi based on the? c? c lucilsulfo-ruokishi base, or halogen atoms shows E1 = When the S 1 ^ = 1 ^ = 1 ^ except in hydrogen atoms =4R = hydrogen atoms, or = methyl and R2= R3R 4= ) in having the structure indicated of claim 7 to feature that the compounds in the heteroasenni must contain chalcogen cyclopropane many polycyclic organic material.

[9] the following expression (11)

[Of 28]


(The R R2, R3and R4and R5, R6, R7, R8 the heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, monovalent substituted heterocycle, oligosaccharide heterocycle 1, monovalent substituents oligosaccharide complex environment on, hydrogen atom, alkyl, alcoi system based, alkylthio, ariiruokishi The ariiruchio based, ariiruarukiru based,? c? c reelalkoxi based, ariiruarukiruchio, aruke - Le base, substituents aruke - Le, archi - Le base, substituents alkynyl, ariru based, amino, amino substituents, azo based, Calvo ethylhexyl, Ashiru based, alkoxicarbo - Le based, formyl, Nitro, shiano based, Siri Le, silyl substituents, Stan - Le, replacing Stan - Le based, boril of Bulgaria based, substituents boril of Bulgaria, Hoth fin base, substituents Hoshino, shiriruokishi based, shiriruokishi substituents, ariirusurufo

-Shows ruoisi, alkylsulfo - ruoisi, or halogen atoms, E1 = S when the 1 ^ = 1 ^ = 1 ^ = 1 ^ = 1 ^ = 1 ^ = 1 ^ = 1 ^ unless a = hydrogen atoms) in having the structure indicated of claim 7 to feature that the compounds in the eteroasenni must include CAL CoGe, cyclopropane many polycyclic organic material.

The following expression (12)

[Of 29]


(Type in the
R2, R3and R4and R5, R6, R7, R8 the heterocycle of ariiru based and ariiru substituents, origoariiru based, substituted origoariiru, 1 on independent, monovalent substituted heterocycle, oligosaccharide heterocycle 1, monovalent substituents oligosaccharide complex environment on, hydrogen atom, alkyl, alcoi system based, alkylthio, ariiruokishi, Ariiruchio based, ariiruarukiru based,? c? c reelalkoxi based, ariiruarukiruchio, aruke - Le base, substituents aruke - Le, archi - Le base, substituents alkynyl, ariru based, amino, amino substituents, azo based, Calvo ethylhexyl, Ashiru based, alkoxicarbo - Le based, formyl, Nitro, shiano based, Siri Le, silyl substituents, Stan - Le, replacing Stan - Le base, boril of Bulgaria, substituents boril of Bulgaria, Hoth Fino, Hoshino substituents, shiriruokishi based, shiriruokishi substituents, ariirusurufo - Show ruokishi, alkylsulfo - ruokishi, or halogen atoms) in indicated, having a structure of claim 7 to feature that the compounds in the heteroasenni must include, Gen cyclopropane many polycyclic organic material.
  • Applicant
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • Inventor
  • YAMAGUCHI SHIGEHIRO
  • OKAMOTO TOSHIHIRO
IPC(International Patent Classification)
Reference ( R and D project ) PRESTO Synthesis and Control AREA
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