WO2012046818A1 - Procédé de production d'un composé polycyclique condensé contenant un chalcogène - Google Patents

Procédé de production d'un composé polycyclique condensé contenant un chalcogène Download PDF

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Publication number
WO2012046818A1
WO2012046818A1 PCT/JP2011/073132 JP2011073132W WO2012046818A1 WO 2012046818 A1 WO2012046818 A1 WO 2012046818A1 JP 2011073132 W JP2011073132 W JP 2011073132W WO 2012046818 A1 WO2012046818 A1 WO 2012046818A1
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group
carbon atoms
formula
compound
atom
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PCT/JP2011/073132
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English (en)
Japanese (ja)
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康生 宮田
善丈 鈴木
柳川　正生
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住友化学株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems

Definitions

  • the compound represented by the formula (5) is represented by the following formula (2a) And a step of oxidizing the compound represented by formula (3a): And a compound represented by the following formula (4a) It is preferable that it is a compound obtained by the method including the process of condensing with the compound represented by these.
  • the compound represented by the above formula (5) includes a step of condensing the compound represented by the above formula (2a) and the compound represented by the above formula (4a), and the following formula (3b) obtained in the above step. It is also preferable that it is a compound obtained by the method including the process of oxidizing the compound (3b) represented by these.
  • each R 10 independently represents a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryloxy group having 6 to 20 carbon atoms.
  • Two R 10 in the molecule may be bonded to form a ring structure together with the boron atom.
  • the present invention also provides each compound represented by the above formula (3a), (3b) or (5) and the following formula (10-3): Each compound represented by is provided.
  • R 12 is the same group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms and an alkoxy group having 1 to 20 carbon atoms, and R 11 , R 13 and R 14 are preferably both hydrogen atoms.
  • R 1 , R 11 , R 12 , R 13 , R 14 , Z 1 and Z 2 are as defined in formula (1), and X 5 independently represents a halogen atom.
  • the reaction can easily proceed in a solution at a temperature of about ⁇ 20 ° C. to 100 ° C.
  • the reaction time is, for example, 10 minutes to 48 hours.
  • the compound (2a) can be obtained by performing general post-treatment and, if necessary, purifying by distillation, recrystallization, silica gel chromatography or the like.
  • leaving groups include leaving groups represented by the following formulas (7), (8) and (9), in addition to the group of formula (6).
  • the compound numbers described in Tables 4 and 5 are (2b-1), (2b-2), (2b-5), (2b-8), (2b-10), ( 2b-12), (2b-13), (2b-15), (2b-17), (2b-19), (2b-30), (2b-33), (2b-38), (2b- 40), (2b-42), (2b-45), (2b-46), (2b-50), or (2b-51). More preferably, the compound numbers are (2b-1), (2b-8), (2b-10), (2b-13), (2b-19), (2b-30), (2b-33), ( 2b-38), (2b-40), (2b-42), (2b-45), (2b-46), (2b-50), or (2b-51).
  • the reaction solvent include water, acetic acid, aromatic hydrocarbon solvents such as benzene, toluene, and xylene, and halogens such as methylene chloride, chloroform, 1,2-dichloroethane, and 1,2-dichloropropane.
  • the hydrocarbon solvent include alcohol solvents such as methanol, ethanol, isopropanol, and n-butanol, and mixed solvents thereof. Alcohol solvents such as methanol, ethanol and isopropanol or acetic acid are preferred, and acetic acid is more preferred.
  • the condensation reaction is performed, for example, in the presence of a transition metal catalyst and a base, for example, about 0 ° C. to 150 ° C.
  • the reaction can easily proceed in the solution within the above temperature range. Since all of the present condensation reactions can be carried out in the above temperature range and at normal pressure, compound (3b) or compound (5) can be obtained in mild conditions and in high yield.
  • nickel catalyst used in the condensation reaction examples include dichlorobis (1,1′-diphenylphosphinoferrocenyl) nickel (II), dichlorobis (diphenylphosphino) nickel (II), dichloronickel (II), and Diiodine nickel (II) is mentioned.
  • reaction solvent examples include aromatic hydrocarbon solvents such as benzene, toluene, and xylene, ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, tert-butyl methyl ether, and ethylene glycol dimethyl ether, N, N -Dimethylformamide and amide solvents such as N, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, and water.
  • a reaction solvent may be used individually by 1 type, and 2 or more types may be mixed and used for it.
  • Examples of the substituent of the “optionally substituted alkyl group having 1 to 30 carbon atoms” in the present embodiment include a fluorine atom and an alkoxy group having 1 to 30 carbon atoms.
  • Examples of the substituent in the “optionally substituted alkoxy group having 1 to 30 carbon atoms” in the present embodiment include a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, and a carbon group having 6 to 30 carbon atoms. Examples thereof include an aryl group, an aralkyl group having 7 to 30 carbon atoms, a heteroaryl group having 4 to 30 carbon atoms, and a heteroaralkyl group having 5 to 30 carbon atoms.
  • the hydrogen atom contained in the substituent may be replaced with a fluorine atom.
  • aryl group of the “aryl group having 6 to 30 carbon atoms which may have a substituent” in the present embodiment a monocyclic or bicyclic aryl group can be exemplified.
  • a preferred aryl group is phenyl. Group, 1-naphthyl group, 2-naphthyl group and the like.
  • the numbers described in Tables 7 to 23 are (4a-1), (4a-2), (4a-3), (4a-6), (4a-8), (4a -11), (4a-13), (4a-15), (4a-16), (4a-17), (4a-20), (4a-21), (4a-24), (4a-26) ), (4a-29), (4a-32), (4a-42), (4a-43), (4a-44), (4a-45), (4a-46), (4a-47), (4a-48), (4a-49), (4a-50), (4a-51), (4a-52), (4a-54), (4a-56), (4a-57), (4a -59), (4a-60), (4a-61), (4a-62), (4a-63), (4a-64), (4a-65), (4a-66), (4a 67), (4a-68), (4a-69), (4a-70), (4a-71), (4a-72), (4a-73), (4a-74), (4a-75) , (4a-76), (4a-77), (4a-
  • Examples of the compound (3b) obtained in Step 2B or Step 2C may further include compounds of the following numbers (3b-446) to (3b-452).
  • Step I ′ in which alkyllithium is reacted with a compound represented by the formula (hereinafter sometimes referred to as “compound (4)”), and Step II in which the reaction product obtained in Step I ′ is alkylsulfided.
  • Step II in which the reaction product obtained in Step I ′ is alkylsulfided.
  • the compound (5) has the numbers (5-1), (5-2), (5-5), (5-6), (5-17), (5-18), (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), (5-140), (5-142), (5-148), (5-150), (5-159), (5-167), (5-177), (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), (5-308), (5-325), (5-327), (5-331), (5-332), (5-375), (5-376), (5- 380), (5-381), (5-399), (5-437), (5-439), or (5-441).
  • the compound (10) can be obtained by performing a usual purification means such as column chromatography, distillation, recrystallization, and recycle gel permeation chromatography as necessary. .
  • Process 4 can proceed under mild conditions.
  • step 4 can be performed at a temperature lower than 100 ° C.
  • the chalcogen-containing polycyclic compound (10) useful as an organic semiconductor material can be produced under milder conditions than before.
  • chalcogen-containing polycyclic compound (10) examples include compounds of numbers (10-1) to (10-445) exemplified in Table 98 to Table 116.
  • Examples of the chalcogen-containing fused polycyclic compound (10) further include compounds of numbers (10-446) to (10-452) represented by the following chemical formulas.
  • the compound (10) has the numbers (10-1), (10-2), (10-5), (10-6), (10-35), (10-37), (10 -81), (10-82), (10-83), (10-84), (10-85), (10-86), (10-87), (10-89), (10-90) ), (10-93), (10-96), (10-98), (10-103), (10-112), (10-177), (10-178), (10-181), (10-184), (10-202), (10-203), (10-207), (10-223), (10-225), (10-230), (10-239), (10 -298), (10-299), (10-300), (10-302), (10-325), (10-327), 10-331), (10-332), (10-375), (10-376), (10-380), is selected from compounds which are (10-381), or (10-399).
  • the reaction solution was added to 103 mL of water, and the precipitated solid was filtered off. After the precipitated solid was washed with water, the obtained solid was dissolved in 90 mL of pyridine, and stirred for 10 hours while heating until the obtained solution was refluxed. After cooling the solution to room temperature, water and chloroform were added to the solution. The obtained organic layer and aqueous layer were separated, and the organic layer was dried over magnesium sulfate and then concentrated to obtain a crude product. The resulting crude product is purified using a silica gel column and gel permeation chromatography to obtain bis (5-hexylbenzo [4,5] thieno) [3,2-c: 2 ′, 3′-e.
  • Step 3A Synthesis of 2,5-bis (4-n-hexylphenyl) -3,4-dimethylsulfinylthiophene Dissolve 2,5-dibromo-3,4-dimethylsulfinylthiophene (0.08 g, 0.2 mmol) in 9 mL of THF. Into the resulting solution, 4-n-hexyl-1- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene (0.17 g, 0.6 mmol), And aqueous cesium carbonate (2.0 M, 2.9 mL) were added.
  • the obtained mixture was bubbled with nitrogen at room temperature, PdCl 2 (dppf) (0.09 g, 0.01 mmol) was added, and the mixture was further heated to 80 ° C. and stirred for 16 hours.
  • the resulting reaction solution was cooled to room temperature, and then an aqueous ammonium chloride solution was added to separate it into an organic layer and an aqueous layer.
  • the product contained in the aqueous layer was extracted with THF and mixed with the organic layer.
  • the combined organic layer was washed with water and saturated aqueous sodium chloride solution, then dried over magnesium sulfate, and concentrated to obtain a crude product.
  • Step 3A Synthesis of 2,5-bis (4-n-pentyloxyphenyl) -3,4-dimethylsulfinylthiophene
  • 2,5-bis (4-n-pentyloxyphenyl) -3,4-dimethylsulfanylthiophene 5 g, 10 mmol
  • 35% aqueous hydrogen peroxide 2.1 g, 22 mmol

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Procédé de production d'un composé polycyclique condensé contenant un chalcogène représenté par la formule (10), qui est caractérisé en ce qu'il comprend une étape consistant à faire réagir un composé représenté par la formule (5) avec un acide.
PCT/JP2011/073132 2010-10-07 2011-10-06 Procédé de production d'un composé polycyclique condensé contenant un chalcogène WO2012046818A1 (fr)

Applications Claiming Priority (4)

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JP2010-227960 2010-10-07
JP2010227960 2010-10-07
JP2011066605A JP5735831B2 (ja) 2010-10-07 2011-03-24 含カルコゲン縮合多環式化合物の製造方法
JP2011-066605 2011-03-24

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012137694A1 (fr) * 2011-04-04 2012-10-11 住友化学株式会社 Procédé de production d'un composé polycyclique condensé contenant des chalcogènes

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05339261A (ja) * 1992-06-03 1993-12-21 Daikin Ind Ltd （ハロアルキル）ジベンゾチオ又はセレノフェニウムハロアルカンスルホナートの製造方法
WO2005087780A1 (fr) * 2004-03-10 2005-09-22 Japan Science And Technology Agency Substance organique polycyclique à anneau fusionné contenant du chalcogénure et son procédé de production
WO2006115305A1 (fr) * 2005-08-18 2006-11-02 Nissan Chemical Industries, Ltd. Compose de thiophene comportant un groupe sulfonyle, et son procede d'obtention
JP2010034449A (ja) * 2008-07-31 2010-02-12 Mitsui Chemicals Inc 有機トランジスタ
WO2010061176A1 (fr) * 2008-11-28 2010-06-03 Cambridge Display Technology Limited Semi-conducteurs organiques

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
JPH05339261A (ja) * 1992-06-03 1993-12-21 Daikin Ind Ltd （ハロアルキル）ジベンゾチオ又はセレノフェニウムハロアルカンスルホナートの製造方法
WO2005087780A1 (fr) * 2004-03-10 2005-09-22 Japan Science And Technology Agency Substance organique polycyclique à anneau fusionné contenant du chalcogénure et son procédé de production
WO2006115305A1 (fr) * 2005-08-18 2006-11-02 Nissan Chemical Industries, Ltd. Compose de thiophene comportant un groupe sulfonyle, et son procede d'obtention
JP2010034449A (ja) * 2008-07-31 2010-02-12 Mitsui Chemicals Inc 有機トランジスタ
WO2010061176A1 (fr) * 2008-11-28 2010-06-03 Cambridge Display Technology Limited Semi-conducteurs organiques

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Title
GAO,P. ET AL.: "Conjugated Ladder-Type Heteroacenes Bearing Pyrrole and Thiophene Ring Units: Facile Synthesis and Characterization", JOURNAL OF ORGANIC CHEMISTRY, vol. 73, no. 23, 2008, pages 9207 - 9213 *
HIRAI,K. ET AL.: "Reactions of P-keto sulfide and sulfoxide with nitrene and diazonium salt", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 19, no. 10, 1971, pages 2207 - 2209 *
IWASAKI,T. ET AL.: "Poly(thiaheterohelicene): A Stiff Conjugated Helical Polymer Comprised of Fused Benzothiophene Rings", ORGANIC LETTERS, vol. 7, no. 5, 2005, pages 755 - 758 *
MCKINNON,D.M. ET AL.: "Fused heterocycles from o-acylbenzenethiol derivatives", CANADIAN JOURNAL OF CHEMISTRY, vol. 66, no. 6, 1988, pages 1405 - 1409 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012137694A1 (fr) * 2011-04-04 2012-10-11 住友化学株式会社 Procédé de production d'un composé polycyclique condensé contenant des chalcogènes

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