JP5600365B2 - キノイドシラフルオレン類の有機半導体材料、該有機半導体材料の製造方法及びその使用 - Google Patents
キノイドシラフルオレン類の有機半導体材料、該有機半導体材料の製造方法及びその使用 Download PDFInfo
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- JP5600365B2 JP5600365B2 JP2013511495A JP2013511495A JP5600365B2 JP 5600365 B2 JP5600365 B2 JP 5600365B2 JP 2013511495 A JP2013511495 A JP 2013511495A JP 2013511495 A JP2013511495 A JP 2013511495A JP 5600365 B2 JP5600365 B2 JP 5600365B2
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- 239000000463 material Substances 0.000 title claims description 100
- 239000004065 semiconductor Substances 0.000 title claims description 78
- 238000004519 manufacturing process Methods 0.000 title claims description 57
- UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 title claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 26
- 239000003960 organic solvent Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 claims description 22
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 20
- -1 dibromo compound Chemical class 0.000 claims description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 16
- 229960001701 chloroform Drugs 0.000 claims description 16
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 15
- 238000006482 condensation reaction Methods 0.000 claims description 14
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 11
- 230000035484 reaction time Effects 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052744 lithium Inorganic materials 0.000 claims description 10
- 229940126062 Compound A Drugs 0.000 claims description 9
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- JPXBIAWPJOGFCF-UHFFFAOYSA-N 4-bromo-1-(4-bromo-2-iodophenyl)-2-iodobenzene Chemical group IC1=CC(Br)=CC=C1C1=CC=C(Br)C=C1I JPXBIAWPJOGFCF-UHFFFAOYSA-N 0.000 claims description 7
- 230000005669 field effect Effects 0.000 claims description 7
- 238000005893 bromination reaction Methods 0.000 claims description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 claims description 3
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- YFTHTJAPODJVSL-UHFFFAOYSA-N 2-(1-benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(SC=C2)C2=C1 YFTHTJAPODJVSL-UHFFFAOYSA-N 0.000 claims 1
- 150000002220 fluorenes Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 39
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- 238000004440 column chromatography Methods 0.000 description 21
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 15
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- 239000000203 mixture Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
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- 239000012312 sodium hydride Substances 0.000 description 8
- 239000012265 solid product Substances 0.000 description 7
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- 101150003085 Pdcl gene Proteins 0.000 description 6
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- JHNMNCSXSSGFLU-UHFFFAOYSA-N CC1(OB(OC1(C)C)C1=[SiH]C=2C(C3=CC(=CC=C3C2C=C1)B1OC(C(O1)(C)C)(C)C)(CCCCCC)CCCCCC)C Chemical compound CC1(OB(OC1(C)C)C1=[SiH]C=2C(C3=CC(=CC=C3C2C=C1)B1OC(C(O1)(C)C)(C)C)(CCCCCC)CCCCCC)C JHNMNCSXSSGFLU-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- WTGUCROFHUIVFJ-UHFFFAOYSA-N CC1(OB(OC1(C)C)C1=[SiH]C=2C(C3=CC(=CC=C3C2C=C1)B1OC(C(O1)(C)C)(C)C)(CCCCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCCCC)C Chemical compound CC1(OB(OC1(C)C)C1=[SiH]C=2C(C3=CC(=CC=C3C2C=C1)B1OC(C(O1)(C)C)(C)C)(CCCCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCCCC)C WTGUCROFHUIVFJ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
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- 238000005859 coupling reaction Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- PDBZUKSMFVSVIR-UHFFFAOYSA-N 2,7-dibromo-9,9-dihexylindeno[2,1-b]siline Chemical compound BrC1=[SiH]C=2C(C3=CC(=CC=C3C=2C=C1)Br)(CCCCCC)CCCCCC PDBZUKSMFVSVIR-UHFFFAOYSA-N 0.000 description 2
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 2
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- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 2
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- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
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- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 2
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- NSDXOHNNRWNSJM-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCCCC)C=1C=C(SC1C=1C=[SiH]C=2C(C3=CC(=CC=C3C2C1)C1=C(C=C(S1)C=1SC=C(C1)CCCCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCCCC)C=1SC=C(C1)CCCCCCCCCCCCCCCCCCCC Chemical compound C(CCCCCCCCCCCCCCCCCCC)C=1C=C(SC1C=1C=[SiH]C=2C(C3=CC(=CC=C3C2C1)C1=C(C=C(S1)C=1SC=C(C1)CCCCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCCCC)C=1SC=C(C1)CCCCCCCCCCCCCCCCCCCC NSDXOHNNRWNSJM-UHFFFAOYSA-N 0.000 description 1
- 0 C*(C(CC(S1)=C(C=C2)C=C(C)C2=C(C=C2)C(**)=CC2=C(C(*)=C2)SC2=C(C=C2C)SC2=C(C#N)C#N)=CC1=C(C=C1*)SC1=C(C#N)C#N)=C Chemical compound C*(C(CC(S1)=C(C=C2)C=C(C)C2=C(C=C2)C(**)=CC2=C(C(*)=C2)SC2=C(C=C2C)SC2=C(C#N)C#N)=CC1=C(C=C1*)SC1=C(C#N)C#N)=C 0.000 description 1
- WYRJUWMPUZCYIP-UHFFFAOYSA-N CC(C)([O-])C.[Th+4].CC(C)([O-])C.CC(C)([O-])C.CC(C)([O-])C Chemical compound CC(C)([O-])C.[Th+4].CC(C)([O-])C.CC(C)([O-])C.CC(C)([O-])C WYRJUWMPUZCYIP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- URQGTLMZBARYTH-UHFFFAOYSA-N S1C(=CC=C1)C=1C=[SiH]C=2C(C3=CC(=CC=C3C2C1)C=1SC=CC1)(CCCCCC)CCCCCC Chemical compound S1C(=CC=C1)C=1C=[SiH]C=2C(C3=CC(=CC=C3C2C1)C=1SC=CC1)(CCCCCC)CCCCCC URQGTLMZBARYTH-UHFFFAOYSA-N 0.000 description 1
- CUBOREGLYVXHQC-UHFFFAOYSA-N S1C(=CC=C1C=1C=[SiH]C=2C(C3=CC(=CC=C3C2C1)C1=CC=C(S1)C=1SC=CC1)(CCCCCC)CCCCCC)C=1SC=CC1 Chemical compound S1C(=CC=C1C=1C=[SiH]C=2C(C3=CC(=CC=C3C2C1)C1=CC=C(S1)C=1SC=CC1)(CCCCCC)CCCCCC)C=1SC=CC1 CUBOREGLYVXHQC-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- NRAYZPGATNMOSB-UHFFFAOYSA-N dichloro(dihexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)CCCCCC NRAYZPGATNMOSB-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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Description
アルカリ性の環境及び触媒、有機溶媒の存在下で、化合物A、B、Cを選択してSuzukiカップリング反応を行い、以下の構造式で表される化合物Eを得る工程と、
触媒、縮合剤及び有機溶媒の存在下で、化合物Eのジブロモ類化合物とマロノニトリルとを縮合反応させ、構造が以下の一般式(I)で表されるキノイドシラフルオレン類の有機半導体材料を得る工程(式中においてm、nは1〜10の間の整数である。)、
あるいは、触媒、縮合剤及び有機溶媒の存在下で、化合物Dとマロノニトリルとを縮合反応させ、構造が以下の一般式(I)で表される前記キノイドシラフルオレン類の有機半導体材料を得る工程と(式中においてm=n=0である。)、
(1)以下の構造式で表される化合物A、B、C、Dをそれぞれ選択する工程と、
(2)アルカリ性の環境及び触媒、有機溶媒の存在下で、化合物A、B、Cを選択してSuzukiカップリング反応を行い、化合物Eを得る工程と(化学反応式は以下の通りである。)、
a)有機溶媒の存在下で、4,4’−ジブロモ−2,2’−ジヨードビフェニルと、リチウムのアルキル誘導体と、ジアルキルジクロロシランとを反応させて、2,7−ジブロモ−9,9−ジアルキルシラフルオレン類化合物を得る工程と(化学反応式は以下の通りである。)、
以下、実施例に基づいて、本発明についてさらに詳細に説明する。
構造式が下述I2に示すようなキノイドシラフルオレン類の有機半導体材料の製造
構造式が下述I3に示すようなキノイドシラフルオレン類の有機半導体材料の製造
図2を参照すると、この太陽電池デバイスは、順に積層されているガラス基板11と、透明陽極12と、中間補助層13と、活性層14と、陰極15とを備えるものである。中間補助層13にポリエチレンジオキシチオフェン:ポリスチレン−スルホン酸複合材料(PEDOT:PSSと略する)を用いている。活性層14は電子供与体材料と電子受容体材料からなり、電子供与体材料に実施例1で製造されたキノイドシラフルオレン類の有機半導体材料を用いている。電子受容体材料は[6,6]フェニル−C61−酪酸メチルエステル(PCBMと略する)であってもよい。透明陽極12にインジウムスズ酸化物(ITOと略する)を用いてもよく、シート抵抗が10−20Ω/sqであるインジウムスズ酸化物を用いると好ましい。陰極15にアルミニウム電極、あるいは例えばCa/AlやBa/Al等の二重金属層電極を用いてもよい。その中で、ガラス基板11を下地とすることができ、製造の際には、ITOガラスを選択して、超音波による洗浄を経た後、酸素−プラズマで処理し、ITOガラスに中間補助層13を塗工して、実施例1で製造されたキノイドシラフルオレン類の有機半導体材料と電子受容体材料とを混合した後中間補助層13に塗工して、活性層14を形成し、その後、真空蒸着技術により活性層14に陰極15を堆積して、上述の太陽電池デバイスを得た。好ましい実施例において、透明陽極12、中間補助層13、活性層14、CaとAlの二重金属層の層厚さはそれぞれ170、40、150、70nmである。
図3を参照すると、順に積層して設けられているガラス基板21と、透明陽極22と、発光層23と、バッファ層24と、陰極25とを備え、実施例1で製造されたキノイドシラフルオレン類の有機半導体材料を用いた有機エレクトロルミネセンスデバイスが示されている。透明陽極22にインジウムスズ酸化物(ITOと略する)を用いてもよい。シート抵抗が10−20Ω/sqであるインジウムスズ酸化物を用いると好ましい。発光層23は、実施例1で製造されたキノイドシラフルオレン類の有機半導体材料からなるものである。バッファ層24にLiFなどを用いてもよいが、これに限定されるものではない。陰極25は、金属Alなどであってもよいが、これらに限定されるものではない。具体的な実施例においては、有機エレクトロルミネセンスデバイスの構造は、ITO/実施例1で製造されたキノイドシラフルオレン類の有機半導体材料/LiF/Alと表される。各層は従来の方法を用いて形成してもよいが、実施例1で製造されたキノイドシラフルオレン類の有機半導体材料は、スピンコーティング技術にてITOに形成してもよい。この発光層に真空蒸着されたLiFバッファ層を用い、バッファ層に蒸着された金属Alを用いてデバイスの陰極とすることができる。
図4を参照すると、この有機電界効果トランジスタは、順に積層して設けられているアンダーレイ31と、絶縁層32と、改質層33と、有機半導体層34と、有機半導体層34に設置されたソース電極35及びドレイン電極36とを備えるものである。その中で、アンダーレイ31は高ドーピングされたシリコンチップ(Si)であってもよいが、これに限定されるものではなく、絶縁層32はマイクロ・ナノメートル(例えば450nm)の厚さのSiO2であってもよいが、これに限定されるものではない。有機半導体層34に実施例1で製造されたキノイドシラフルオレン類の有機半導体材料を用いている。ソース電極35及びドレイン電極36に金を用いてもよいが、これに限定されるものではない。改質層33は、オクタデシルトリクロロシラン(OTS)であってもよいが、これに限定されるものではない。アンダーレイ31と、絶縁層32と、改質層33と、ソース電極35及びドレイン電極36のすべてを従来の方法で形成してもよい。有機半導体層34は実施例1で製造されたキノイドシラフルオレン類の有機半導体材料を、10−4Paに近い真空度で、改質層33により改質された絶縁層32にスピンコーティングしてなるものであってもよい。
Claims (10)
- 前記R1、R2、R5、R6は−H、−C6H13又は−C20H41のアルキル基から選ばれるものであり、R3、R4は−CH3、−C6H13又は−C20H41のアルキル基から選ばれるものである、
ことを特徴とする請求項1に記載のキノイドシラフルオレン類の有機半導体材料。 - 以下の構造式で表される化合物A、B、C、Dを選択する工程と、
アルカリ性の環境及び触媒、有機溶媒の存在下で、化合物A、B、Cを選択してSuzukiカップリング反応を行い、以下の構造式で表される化合物Eを得る工程と、
触媒、縮合剤及び有機溶媒の存在下で、化合物Eのジブロモ類化合物とマロノニトリルとを縮合反応させ、構造が以下の一般式(I)で表されるキノイドシラフルオレン類の有機半導体材料を得る工程(式中において、m、nは1〜10の間の整数である。)、
あるいは、触媒、縮合剤及び有機溶媒の存在下で、化合物Dとマロノニトリルとを縮合反応させ、構造が以下の一般式(I)で表される前記キノイドシラフルオレン類の有機半導体材料を得る工程と(式中において、m=n=0である。)、
- 前記化合物Aの製造方法は、
有機溶媒の存在下で、4,4’−ジブロモ−2,2’−ジヨードビフェニルと、リチウムのアルキル誘導体と、ジアルキルジクロロシランとを反応させて、2,7−ジブロモ−9,9−ジアルキルシラフルオレン類化合物を得る工程と、
有機溶媒の存在下で、2,7−ジブロモ−9,9−ジアルキルシラフルオレン類化合物と、リチウムのアルキル誘導体と、2−イソプロポキシ−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランとを縮合反応させ、化合物Aを得る工程とを含む、
ことを特徴とする請求項3に記載のキノイドシラフルオレン類の有機半導体材料の製造方法。 - 前記2,7−ジブロモ−9,9−ジアルキルシラフルオレン類化合物の製造工程において、前記4,4’−ジブロモ−2,2’−ジヨードビフェニルと、リチウムのアルキル誘導体と、ジアルキルジクロロシランとの三つの反応物のモル比は、1.0:2.0〜4.0:2.0〜4.0であり、
前記2,7−ジブロモ−9,9−ジアルキルシラフルオレン類化合物の製造中の反応温度は、−100〜−25℃であり、反応時間は、24〜48時間であり、
前記2,7−ジブロモ−9,9−ジアルキルシラフルオレン類化合物の製造工程において、前記有機溶媒は、テトラヒドロフラン、エチルエーテル、ジクロロメタン、トリクロロメタン、エチルアセテートの内の少なくとも1種である、
ことを特徴とする請求項4に記載のキノイドシラフルオレン類の有機半導体材料の製造方法。 - 前記縮合反応工程における前記2,7−ジブロモ−9,9−ジアルキルシラフルオレン化合物と、リチウムのアルキル誘導体と、2−イソプロポキシ−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランとの三つの反応物のモル比は、1.0:2.0〜4.0:2.0〜4.0であり、
前記縮合反応の反応温度は、−100℃〜−25℃であり、反応時間は、24〜48時間であり、
前記縮合反応工程における前記有機溶媒は、テトラヒドロフラン、エチルエーテル、ジクロロメタン、トリクロロメタン、エチルアセテートの内の少なくとも1種である、
ことを特徴とする請求項4に記載のキノイドシラフルオレン類の有機半導体材料の製造方法。 - 前記Suzukiカップリング反応工程において、
前記化合物A、B、Cの三つの反応物のモル比は、1.0:1.0〜1.5:1.0〜1.5であり、
前記Suzukiカップリング反応の反応温度は、75〜120℃であり、反応時間は、12〜72時間であり、
前記アルカリ性環境のアルカリは、NaOH、Na2CO3、NaHCO3、テトラエチルアンモニウムハイドロキサイドの内の少なくとも1種であり、
前記触媒は、Pd(PPh3)4、Pd2(dba)3/P(o−Tol)3、Pd(PPh3)2Cl2の内の少なくとも1種であって、その使用量は、モル百分率で化合物Aの0.05%〜20%であり、
前記有機溶媒は、エチレングリコールジメチルエーテル、テトラヒドロフラン、エチルエーテル、ジクロロメタン、トリクロロメタン又はエチルアセテートの内の少なくとも1種である、
ことを特徴とする請求項3に記載のキノイドシラフルオレン類の有機半導体材料の製造方法。 - 前記臭素化反応工程において、
前記化合物EとN−ブロモスクシンイミドとのモル比は、1.0:2.0〜2.5であり、
前記臭素化反応の反応温度は、−5〜30℃であり、反応時間は、12〜48時間であり、
前記有機溶媒は、N,N−ジメチルフォルムアミド、テトラヒドロフラン、エチルエーテル、ジクロロメタン、トリクロロメタン、エチルアセテート、酢酸の内の少なくとも1種である、
ことを特徴とする請求項3に記載のキノイドシラフルオレン類の有機半導体材料の製造方法。 - 前記縮合反応工程において、
前記化合物Eのジブロモ類化合物とマロノニトリルとのモル比は、1.0:2.0〜10であり、
前記縮合反応の反応温度は、75〜120℃であり、反応時間は12〜72時間であり、
前記有機溶媒は、エチレングリコールジメチルエーテル、テトラヒドロフラン、エチルエーテル、ジクロロメタン、トリクロロメタン又はエチルアセテートの内の少なくとも1種であり、
前記触媒は、有機パラジウムであって、その使用量は、モル百分率で化合物Eのジブロモ類化合物の0.05%〜20%であり、
前記縮合剤は、NaH、ナトリウムアルコキシドの内の少なくとも1種である、
ことを特徴とする請求項3に記載のキノイドシラフルオレン類の有機半導体材料の製造方法。 - 請求項1に記載のキノイドシラフルオレン類の有機半導体材料の、有機光電材料、ポリマー太陽電池、有機エレクトロルミネセンスデバイス、有機電界効果トランジスタ、有機光記憶デバイス、有機非線形材料又は/及び有機レーザーにおける使用。
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