JP5524043B2 - 置換されたペンタセン類の調製方法 - Google Patents
置換されたペンタセン類の調製方法 Download PDFInfo
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- JP5524043B2 JP5524043B2 JP2010503370A JP2010503370A JP5524043B2 JP 5524043 B2 JP5524043 B2 JP 5524043B2 JP 2010503370 A JP2010503370 A JP 2010503370A JP 2010503370 A JP2010503370 A JP 2010503370A JP 5524043 B2 JP5524043 B2 JP 5524043B2
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- JP
- Japan
- Prior art keywords
- tetrasubstituted
- pentacene
- disubstituted
- isobenzofuran
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000000034 method Methods 0.000 title claims description 54
- 150000002964 pentacenes Chemical class 0.000 title claims description 23
- 230000008569 process Effects 0.000 title description 14
- 238000002360 preparation method Methods 0.000 title description 4
- -1 1,4,8,11-tetrasubstituted pentacene Chemical class 0.000 claims description 141
- 239000000463 material Substances 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 35
- 239000004065 semiconductor Substances 0.000 claims description 33
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 22
- 239000003153 chemical reaction reagent Substances 0.000 claims description 21
- 238000009472 formulation Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 14
- 239000010408 film Substances 0.000 claims description 13
- 238000005401 electroluminescence Methods 0.000 claims description 12
- 230000003287 optical effect Effects 0.000 claims description 11
- 239000007800 oxidant agent Substances 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000013086 organic photovoltaic Methods 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical class C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 5
- 238000006117 Diels-Alder cycloaddition reaction Methods 0.000 claims description 5
- 230000005669 field effect Effects 0.000 claims description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000003990 capacitor Substances 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 230000001035 methylating effect Effects 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 238000000018 DNA microarray Methods 0.000 claims description 2
- 238000005034 decoration Methods 0.000 claims description 2
- 239000007772 electrode material Substances 0.000 claims description 2
- 239000011888 foil Substances 0.000 claims description 2
- 150000001247 metal acetylides Chemical class 0.000 claims description 2
- 239000012788 optical film Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000010410 layer Substances 0.000 description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
- 239000000047 product Substances 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 11
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 150000002596 lactones Chemical class 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 8
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
- FIYYMXYOBLWYQO-UHFFFAOYSA-N ortho-iodylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I(=O)=O FIYYMXYOBLWYQO-UHFFFAOYSA-N 0.000 description 8
- IGKLGCQYPZTEPK-UHFFFAOYSA-N pentacene-1,2-dione Chemical compound C1=CC=C2C=C(C=C3C(C=C4C=CC(C(C4=C3)=O)=O)=C3)C3=CC2=C1 IGKLGCQYPZTEPK-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- TVAVCYUNZIELEP-UHFFFAOYSA-N triethyl-[2-[1,4,8,11-tetramethyl-13-(2-triethylsilylethynyl)pentacen-6-yl]ethynyl]silane Chemical compound C1=CC(C)=C2C=C3C(C#C[Si](CC)(CC)CC)=C(C=C4C(C(C)=CC=C4C)=C4)C4=C(C#C[Si](CC)(CC)CC)C3=CC2=C1C TVAVCYUNZIELEP-UHFFFAOYSA-N 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 235000019994 cava Nutrition 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 238000007641 inkjet printing Methods 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- VABDMWRXHBJBEO-UHFFFAOYSA-N 4,7-dimethyl-2-benzofuran Chemical compound CC1=CC=C(C)C2=COC=C12 VABDMWRXHBJBEO-UHFFFAOYSA-N 0.000 description 5
- JNXGHQDZQVYCKB-UHFFFAOYSA-N 4,7-dimethyl-3h-2-benzofuran-1-one Chemical compound CC1=CC=C(C)C2=C1COC2=O JNXGHQDZQVYCKB-UHFFFAOYSA-N 0.000 description 5
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 5
- 238000005698 Diels-Alder reaction Methods 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000002800 charge carrier Substances 0.000 description 5
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- 150000002009 diols Chemical class 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
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- 230000002378 acidificating effect Effects 0.000 description 4
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- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
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- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CBTHYYQGYFXUEO-UHFFFAOYSA-N 1,4,8,11-tetramethylpentacene-6,13-dione Chemical compound C1=CC(C)=C2C=C(C(=O)C3=C(C=C4C(C)=CC=C(C4=C3)C)C3=O)C3=CC2=C1C CBTHYYQGYFXUEO-UHFFFAOYSA-N 0.000 description 3
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- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
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- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
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- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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- 229940116411 terpineol Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
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- 238000007740 vapor deposition Methods 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Description
または
a2)酸化剤の存在下で1,2−ビス(ヒドロキシメチル)−3,6−二置換ベンゼン(3)を酸化して、4,7−二置換3H−イソベンゾフラン−1−オン(4)を形成し、
または
a3)酸化剤の存在下で1,2−ビス(ヒドロキシメチル)−3,6−二置換ベンゼン(3)を酸化して、4,7−二置換1−ヒドロキシ−1,3−ジヒドロ−イソベンゾフラン(5a)を形成し、
および、工程a1)または工程a2)の場合、
b)還元剤の存在下で工程a1)またはa2)の生成物(4)を還元して、4,7−二置換1−ヒドロキシ−1,3−ジヒドロ−イソベンゾフラン(5a)を形成し、
および
c)工程a3)またはb)の生成物(5a)をメチル化して、4,7−二置換1−メトキシ−1,3−ジヒドロ−イソベンゾフラン(5b)を形成し、
d)塩基の存在下で工程c)の生成物(5b)を脱離して、4,7−二置換イソベンゾフラン(6)を形成し、
e)ディールス−アルダー環化付加により工程d)の生成物(6)をp−ベンゾキノンと反応して、ビス環状付加物(7)を形成し、
f)塩基の存在下で工程e)の生成物(7)を脱水して、1,4,8,11−四置換6,13−ペンタセンキノン(8)を形成し、
g)一置換金属アセチリドで工程f)の生成物(8)をアルキネート化して、1,4,8,11−四置換6,13−ビス(1−置換エチニル)ペンタセン(9)を形成する。
2種類の出発材料、即ち、工程a1)において使用される4,7−二置換イソベンゾフラン−1,3−ジオン(2)および工程a2)またはa3)において使用される1,2−ビス(ヒドロキシメチル)−3,6−二置換ベンゼン(3)の合成は、文献3[非特許文献6]において既に報告された。その工程は、ディールス−アルダー反応[非特許文献6、非特許文献7]、結果として生じる環状付加物1の酸で触媒された脱水[非特許文献6、非特許文献7]、および無水物2のジオール3への還元[非特許文献6、非特許文献8]である。
x1)ディールス−アルダー環化付加により2,5−二置換フランを無水マレイン酸と反応して、環状付加物(1)を形成し、
x2)酸の存在下で工程x1)の生成物(1)を脱水して、4,7−二置換イソベンゾフラン−1,3−ジオン(2)を形成し、
および、(3)を調製する場合、
x3)水素化試薬の存在下で工程x2)の生成物(2)を還元して、1,2−ビス(ヒドロキシメチル)−3,6−二置換ベンゼン(3)を形成する。
2通りの方法により、無水物2をラクトン4へ選択的に還元できる。初めは、より選択的な還元剤、好ましくは、例えば、水素化ホウ素ナトリウムなどの水素化剤を使用して効果的に還元する[非特許文献9]。あるいは、Rainboltら[非特許文献11]によって記載される通りのYang−Zhu還元[非特許文献10]の変法を使用し、酢酸中で亜鉛を使用して100℃で無水物2を還元し、ラクトン4を生じる。
先に報告されたジオール3[非特許文献6、非特許文献8]からの次の工程は、例えば、酸化マンガン(IV)などの酸化剤を使用する酸化で、Hiranoらの方法を基礎としており、この方法により3H−イソベンゾフラン−1−オンが調製された[非特許文献12]。所望のラクトン生成物4への転化を完了するために、好ましくは、大過剰、典型的には10当量の酸化剤を使用する。より少量の酸化剤を使用すると、ラクトンおよびラクトール生成物の混合物が得られる。
Coreyらによって記載される方法を使用してジオール3をラクトン5aに選択的に酸化でき、酸化剤として2−ヨードキシ安息香酸(IBX)を使用する[非特許文献15]。典型的には、3などの1,4−ジオールについては、ラクトンへの更なる酸化は大した程度は起きない[非特許文献15]。
還元剤の存在下においてラクトン4をラクトール5aに選択的に還元し、続いて、Rainboltらによって記載され、−60℃で水素化ジイソブチルアルミニウムを使用し[非特許文献11]、Rodrigo条件[非特許文献13]としても知られている方法を行う。単離後、例えば、ボロントリフルオリドジエチルエーテラートなどのルイス酸触媒の存在下において、ラクトール5aを、例えば、メタノールなどのメチル化剤と反応し、メチル化されたラクトール5bを生じ、続いて、Manらの方法を行い、この様にして、1−メトキシ−1,3−ジヒドロイソベンゾフランを調製する[非特許文献14]。
イソベンゾフランを調製するためにNaitoおよびRickborn[非特許文献16]によって報告されたものに類似の様式において、メチル化されたラクトール5bより、リチウムジイソプロピルアミドで処理することにより、不可欠なイソベンゾフラン中間体である4,7−ジメチル−イソベンゾフラン6を形成する。また、酸性条件下において2−(ジメトキシメチル)ベンジルアルコールよりイソベンゾフランを形成する方法が、SmithおよびDibbleによっても報告された[非特許文献5]。イソベンゾフラン6は比較的安定であり、同様の誘導体の安定性が報告されているが[非特許文献17]、いずれにせよ、濃縮して乾燥するよりもむしろ希釈された溶液中においてイソベンゾフラン6を保存し、可能な限り早急に、引き続くディールス−アルダー反応において使用する。ディールス−アルダー反応においては、イソベンゾフラン6をp−ベンゾキノンと反応して、ビス環状付加物7を生じる。酸性条件を使用するDibbleおよびSmithの報告[非特許文献5]と異なり、本発明においては、単離された生成物は依然としてエポキシ架橋を含有しており、脱水されペンタセンキノン生成物を生じることはない。
エポキシ架橋を除去してペンタセンキノン8を調製するために、Wongら[非特許文献13]によって報告されたものに類似の様式において、メタノール中で酢酸ナトリウムを使用し、穏和な塩基性条件下において、ビス環状付加物7を脱水する。マイクロ波反応器において、溶媒の沸点(160℃)より高温で反応を行うと、還流温度における長時間の反応時間と反対に、短い反応時間(5分)で生成物への高い転化が得られることが見出された。この脱水を、0℃で濃硫酸[非特許文献7]および還流メタノール中で濃塩酸[非特許文献19]を使用する酸性条件下で行うよう尽力したが、両者とも成功しなかった。
最後に、Anthonyおよび共同研究者ら[非特許文献4]によって記載されるものに類似の様式において、トリアルキルシリルアセチレンおよびn−ブチルリチウムより、その場で形成されるリチウムトリアルキルシリルアセチリド(例えば、アルキルはエチル)と反応することにより、ペンタセンキノン8のアルキネート化を実行する。次いで、Anthonyおよび共同研究者ら[非特許文献3]によって記載されるものに類似の様式において、中間体種を塩化スズ(II)の酸性化された飽和水溶液で処理し、最終生成物材料である1,4,8,11−テトラメチル−6,13−ビス(トリアルキルシリルエチニル)ペンタセン9を与える。あるいは、Anthonyおよび共同研究者ら[非特許文献4]によって記載されるものに類似の様式において、アリールアセチレンおよびn−ブチルリチウムより、その場で形成されるリチウムアリールアセチリドとペンタセンキノン8を反応させることにより、ペンタセン種にアリールアセチレン構造成分を導入できる。
Xは、SiR5R6R7またはArであり、
R1〜7は、同一または異なるカルビルまたはヒドロカルビル基であり、
Arは、出現する毎に互いに独立に、置換されていてもよいアリールまたはヘテロアリール基である。
R0およびR00は、それぞれ互いに独立に、Hまたは1〜12個のC原子のアルキルであり、
Y1およびY2は、それぞれ互いに独立に、H、F、ClまたはCNである。
−ソース電極(4)と、
−ドレイン電極(4)と、
−ゲート電極(2)と、
−有機半導体(OSC)層(5)と、
−1つ以上のゲート絶縁体層(3)と、
−任意要素として基体(1)と
を含み、
ただし、OSC層は、本発明による1種類以上の置換されたペンタセン化合物を含む。
−低仕事関数電極(例えば、アルミニウム)と、
−高仕事関数電極(例えば、ITO)とで、その一方は透明であり、
−正孔輸送および電子輸送材料からなる二重層とで;二重層は2つの区別される層、または調合混合物として存在してよく(例えば、Coakley、K.M.およびMcGehee、M.D.Chem.Mater.2004年、16巻、4533頁参照)、
−正孔にオームコンタクトを与えるために高仕事関数電極の仕事関数を修正するための任意構成である導電性ポリマー層(例えば、PEDOT:PSSなど)と、
−電子にオームコンタクトを与えるための高仕事関数電極上の任意構成である被膜(LiFなど)と、
を含む。
ある。
1,4,8,11−テトラメチル−6,13−ビス(トリエチルシリルエチニル)ペンタセン(9)を下に記載される通り調製する。
図6で例示される通りのトップゲートOFET装置を、国際特許出願公開第2005/055248号パンフレットに記載される通りに調製する。例1の化合物(9)を、バインダー材料であるポリ(アルファ−メチルスチレン)と共に(1:1比)、総固形分4%でテトラリン中に溶解する。結果として生じる溶液を、PEN基体上のマスクされたPt/Pdのパターン化ソース/ドレイン電極上にスピンコートする。誘電材料の溶液であるLisicon(登録商標)D139(メルク社、ダルムスタット市、ドイツ国より商業的に入手可)を、ゲート絶縁体層として使用する。被覆され乾燥されたゲート絶縁体層の上に、金製ゲートコンタクトをシャドーマスクを通して蒸発させることで形成する。
μlin=6.3cm2/Vs(線移動度)
Ion/Ioff=7×103 (電流オン/オフ比)。
Claims (18)
- 1,4,8,11−四置換ペンタセンを調製する方法であって、
a1)還元剤の存在下で4,7−二置換イソベンゾフラン−1,3−ジオン(2)を還元して、4,7−二置換3H−イソベンゾフラン−1−オン(4)を形成し、
または
a2)酸化剤の存在下で1,2−ビス(ヒドロキシメチル)−3,6−二置換ベンゼン(3)を酸化して、4,7−二置換3H−イソベンゾフラン−1−オン(4)を形成し、
または
a3)酸化剤の存在下で1,2−ビス(ヒドロキシメチル)−3,6−二置換ベンゼン(3)を酸化して、4,7−二置換1−ヒドロキシ−1,3−ジヒドロ−イソベンゾフラン(5a)を形成し、
および、工程a1)または工程a2)の場合、
b)還元剤の存在下で工程a1)またはa2)の生成物(4)を還元して、4,7−二置換1−ヒドロキシ−1,3−ジヒドロ−イソベンゾフラン(5a)を形成し、
および
c)工程a3)またはb)の生成物(5a)をメチル化して、4,7−二置換1−メトキシ−1,3−ジヒドロ−イソベンゾフラン(5b)を形成し、
d)塩基の存在下で工程c)の生成物(5b)からメタノールを脱離して、4,7−二置換イソベンゾフラン(6)を形成し、
e)ディールス−アルダー環化付加により工程d)の生成物(6)をp−ベンゾキノンと反応して、ビス環状付加物(7)を形成し、
f)塩基の存在下で工程e)の生成物(7)を脱水して、1,4,8,11−四置換6,13−ペンタセンキノン(8)を形成し、
g)一置換金属アセチリドで工程f)の生成物(8)をアルキネート化して、1,4,8,11−四置換6,13−ビス(1−置換エチニル)ペンタセン(9)を形成する
ことによる方法。 - 工程a1)の遊離物(2)および工程a2)およびa3)の遊離物(3)を以下の工程:
x1)ディールス−アルダー環化付加により2,5−二置換フランを無水マレイン酸と反応して、環状付加物(1)を形成し、
x2)酸の存在下で工程x1)の生成物(1)を脱水して、4,7−二置換イソベンゾフラン−1,3−ジオン(2)を形成し、
および、(3)を調製する場合、
x3)水素化試薬の存在下で工程x2)の生成物(2)を還元して、1,2−ビス(ヒドロキシメチル)−3,6−二置換ベンゼン(3)を形成する
ことで調製することを特徴とする請求項1に記載の方法。 - Ar1、2は、4−アルキルフェニルまたは2,4,6−トリアルキルフェニルより選択されることを特徴とする請求項4に記載の方法。
- R 1〜4 は、それぞれ互いに独立に、メチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、ヘプチル、オクチルおよびFより選択されることを特徴とする請求項3〜5のいずれか1項に記載の方法。
- SiR 5 R 6 R 7 は、tert−ブチルジメチルシリル(R 5 =R 6 =Me、R 7 =t−Bu)、トリメチルシリル(R 5 =R 6 =R 7 =Me)、トリイソプロピルシリル(R 5 =R 6 =R 7 =i−Pr)およびトリエチルシリル(R 5 =R 6 =R 7 =Et)より選択されることを特徴とする請求項4〜6のいずれか1項に記載の方法。
- Ar 1、2 は、4−アルキルフェニルまたは2,4,6−トリアルキルフェニルより選択されることを特徴とする請求項9に記載の1,4,8,11−四置換ペンタセン。
- R 1〜4 は、それぞれ互いに独立に、メチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、ヘプチル、オクチルおよびFより選択されることを特徴とする請求項8〜10のいずれか1項に記載の1,4,8,11−四置換ペンタセン。
- SiR 5 R 6 R 7 は、tert−ブチルジメチルシリル(R 5 =R 6 =Me、R 7 =t−Bu)、トリメチルシリル(R 5 =R 6 =R 7 =Me)、トリイソプロピルシリル(R 5 =R 6 =R 7 =i−Pr)およびトリエチルシリル(R 5 =R 6 =R 7 =Et)より選択されることを特徴とする請求項9〜11のいずれか1項に記載の1,4,8,11−四置換ペンタセン。
- 請求項8〜12のいずれか1項に記載の1種類以上の1,4,8,11−四置換ペンタセンおよび1種類以上の溶媒を含む配合物。
- 請求項8〜12のいずれか1項に記載の1種類以上の1,4,8,11−四置換ペンタセンと、1種類以上の有機バインダーまたはそれの前駆体と、任意成分として1種類以上の溶媒とを含む配合物。
- 光学的、電気光学的、電子、エレクトロルミネッセンス(EL)またはフォトルミネッセンス性部品または装置における電荷輸送、半導体、導電、光導電または発光材料としての請求項8〜12のいずれか1項に記載の1,4,8,11−四置換ペンタセンまたは請求項13または14に記載の配合物の使用。
- 請求項8〜12のいずれか1項に記載の1,4,8,11−四置換ペンタセンまたは請求項13または14に記載の配合物を含む電荷輸送、半導体、導電、光導電または発光材料または部品。
- 請求項8〜12のいずれか1項に記載の1,4,8,11−四置換ペンタセン、請求項13または14に記載の配合物、または、請求項16に記載の材料または部品を含む光学的、電気光学的または電子部品または装置。
- 請求項17に記載の部品または装置であって、それは、電気光学的ディスプレイ、LCD、光学フィルム、リターダー、コンペンセーター、偏光子、ビームスプリッター、反射フィルム、配向層、カラーフィルター、ホログラフィック素子、ホットスタンプ箔、着色画像、装飾またはセキュリティーマーク、LC顔料、接着剤、非線形光学(NLO)装置、光学情報記憶装置、電子装置、有機半導体、有機電界効果トランジスタ(OFET)、集積回路(IC)、薄膜トランジスタ(TFT)、無線識別(RFID)タグ、有機発光ダイオード(OLED)、有機発光トランジスタ(OLET)、エレクトロルミネッセンス(EL)ディスプレイ、有機光起電(OPV)装置、有機太陽電池(O−SC)、有機レーザーダイオード(O−レーザー)、有機集積回路(O−IC)、照明装置、センサー装置、電極材料、光導電体、光検出器、電子写真記録装置、キャパシタ、電荷注入層、ショットキーダイオード、平坦化層、帯電防止フィルム、導電性基材、導電性パターン、光導電体、電子写真用途、電子写真記録、有機記憶装置、バイオセンサー、バイオチップより選択されることを特徴とする部品または装置。
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