JP5774599B2 - ジチエノベンゾ−チエノ[3,2−b]チオフェン−コポリマーとその溶液加工可能な高機能性半導電性ポリマーとしての利用 - Google Patents
ジチエノベンゾ−チエノ[3,2−b]チオフェン−コポリマーとその溶液加工可能な高機能性半導電性ポリマーとしての利用 Download PDFInfo
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- 229920000642 polymer Polymers 0.000 title claims description 16
- 229920001577 copolymer Polymers 0.000 title claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 239000004065 semiconductor Substances 0.000 claims description 34
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- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 238000007639 printing Methods 0.000 claims description 14
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
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- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
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- LNFFEPHGAMYIEY-UHFFFAOYSA-N 9-tetradecyl-5,10,14,18-tetrathiapentacyclo[10.6.0.02,6.07,11.013,17]octadeca-1(12),2(6),3,7(11),8,13(17),15-heptaene Chemical compound C(CCCCCCCCCCCCC)C1=CC2=C3C(=C4C(=C2S1)C=1SC=CC=1S4)C=CS3 LNFFEPHGAMYIEY-UHFFFAOYSA-N 0.000 description 4
- AKQULYXNABFILT-UHFFFAOYSA-N C[Sn](C)(C)C(C1=C2C=CS1)=C[S+]2[Sn](C)(C)C Chemical compound C[Sn](C)(C)C(C1=C2C=CS1)=C[S+]2[Sn](C)(C)C AKQULYXNABFILT-UHFFFAOYSA-N 0.000 description 4
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- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- UAAIFJLYKGNHDL-UHFFFAOYSA-N CCCCCCCCCCCCCCC1=CSC2=C1SC1=C(C=C[S+]3CCCCCCCCCCCCCC)C3=C(C=CS3)C3=C21 Chemical compound CCCCCCCCCCCCCCC1=CSC2=C1SC1=C(C=C[S+]3CCCCCCCCCCCCCC)C3=C(C=CS3)C3=C21 UAAIFJLYKGNHDL-UHFFFAOYSA-N 0.000 description 2
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
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- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
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- 239000003599 detergent Substances 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 150000002467 indacenes Chemical class 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000005468 ion implantation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000005482 norpinyl group Chemical group 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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Description
piは、必要に応じて1〜4個のRa基で置換された単環基または多環基であり、
式中
Raは、それぞれ独立して、水素、a)ハロゲン、b)−CN、c)−NO2、d)オキソ、e)−OH、f)=C(Rb)2、g)C1-20アルキル基、h)C2-20アルケニル基、i)C2-20アルキニル基、j)C1-20アルコキシ基、k)C1-20アルキルチオ基、l)C1-20ハロアルキル基、m)−Y−C3-10シクロアルキル基、n)−Y−C6-14アリール基、o)−Y−3−12員環シクロヘテロアルキル基、またはp)−Y−5−14員環ヘテロアリール基であり(上記のC1-20アルキル基とC2-20アルケニル基、C2-20アルキニル基、C3-10シクロアルキル基、C6-14アリールまたはハロアリール基、3−12員環シクロヘテロアルキル基、5−14員環ヘテロアリール基は、必要に応じて1〜4個のRb基で置換されていてもよい);
Rbは、それぞれ独立して、a)ハロゲン、b)−CN、c)−NO2、d)オキソ、e)−OH、f)−NH2、g)−NH(C1-20アルキル)、h)−N(C1-20アルキル)2、i)−N(C1-20アルキル)−C6-14アリール、j)−N(C6-14アリール)2、k)−S(O)mH、l)−S(O)m-C1-20アルキル、m)−S(O)2OH、n)−S(O)m-OC1-20アルキル、o)−S(O)m-OC6-14アリール、p)−CHO、q)−C(O)−C1-20アルキル、r)−C(O)−C6-14アリール、s)−C(O)OH、t)−C(O)−OC1-20アルキル、u)−C(O)−OC6-14アリール、v)−C(O)NH2、w)−C(O)NH−C1-20アルキル、x)−C(O)N(C1-20アルキル)2、y)−C(O)NH−C6-14アリール、z)−C(O)N(C1-20アルキル)−C6-14アリール、aa)−C(O)N(C6-14アリール)2、ab)−C(S)NH2、ac)−C(S)NH−C1-20アルキル、ad)−C(S)N(C1-20アルキル)2、ae)−C(S)N(C6-14アリール)2、af)−C(S)N(C1-20アルキル)−C6-14アリール、ag)−C(S)NH−C6-14アリール、ah)−S(O)mNH2、ai)−S(O)mNH(C1-20アルキル)、aj)−S(O)mN(C1-20アルキル)2、ak)−S(O)mNH(C6-14アリール)、al)−S(O)mN(C1-20アルキル)−C6-14アリール、am)−S(O)mN(C6-14アリール)2、an)SiH3、ao)SiH(C1-20アルキル)2、ap)SiH2(C1-20アルキル)、ar)−Si(C1-20アルキル)3、as)C1-20アルキル基、at)C2-20アルケニル基、au)C2-20アルキニル基、av)C1-20アルコキシ基、aw)C1-20アルキルチオ基、ax)C1-20ハロアルキル基、ay)C3-10シクロアルキル基、az)C6-14アリールまたはハロアリール基、ba)3−12員環シクロヘテロアルキル基、またはbb)5−14員環ヘテロアリール基であり;
Yは、それぞれ独立して、2価のC1-6アルキル基、2価のC1-6ハロアルキル基、または共有結合であり;
mは、それぞれ独立して0、1または2であり;
R1とR2とR3はそれぞれ、独立してH、ハロゲン、CN、C1-30アルキル基、C2-30アルケニル基、C1-30ハロアルキル基、C2-30アルキニル基、C1-30アルコキシ基、C(O)−C1-20アルキル基、C(O)−OC1-20アルケニル基、Y−C3-10シクロアルキル基、−Y−3−12員環シクロヘテロアルキル基(これらはそれぞれ、ハロゲンと−CN、C1-6アルキル基、C1-6アルコキシ基、C1-6ハロアルキル基から選ばれる1〜5個の置換基で置換されていてもよい)、−L−Ar1、−L−Ar1−Ar1、−L−Ar1−R4、または−L−Ar1−Ar1−R4であり
[式中、Lは、それぞれ独立して、−O−、−Y−O−Y−、−S−、−S(O)−、−Y−S−Y−、−C(O)−、−NRcC(O)−、−NRc−、−SiRc 2−、−Y−[SiRc 2]−Y−、2価のC2-30アルキル基、2価のC1-30アルケニル基、2価のC1-30ハロアルキル基、または共有結合である;
(式中、Rcはそれぞれ、H、C1-20アルキル基、または−Y−C6-14アリール基であり;Ar1は、それぞれ独立して、C6-14アリール基または5−14員環ヘテロアリール基であり、これらの基は、必要ならハロゲンと−CN、C1-6アルキル基、C1-6アルコキシ基、C1-6ハロアルキル基から選ばれる1〜5個の置換基で置換されていてもよい);
R4は、それぞれ独立して、C1-20アルキル基、C2-20アルケニル基、C1-20ハロアルキル基、C1-20アルコキシ基、−L’−Ar2、−L’−Ar2−Ar2、−L’−Ar2−R5、または−L’−Ar2−Ar2−R5であり;
(式中、L’は、それぞれ独立して、−O−、−Y−O−Y−、−S−、−S(O)−、−Y−S−Y−、−C(O)−、−NRcC(O)−、−NRc−、−SiRc 2−、−Y−[SiRc 2]−Y−、2価のC1-20アルキル基、2価のC1-20アルケニル基、2価のC1-20ハロアルキル基、または共有結合であり;
Ar2は、それぞれ独立して、C6-14アリール基または5−14員環ヘテロアリール基であり、各基は必要に応じてハロゲンと−CN、C1-6アルキル基、C1-6アルコキシ基、C1-6ハロアルキル基から選ばれる1〜5個の置換基で置換されていてもよい;
R5はそれぞれ、C1-20アルキル基、C2-20アルケニル基、C1-20ハロアルキル基、またはC1-20アルコキシ基であり;
Yは、それぞれ独立して、2価のC1-6アルキル基、2価のC1-6ハロアルキル基、または共有結合である)];
n=0、1、2であり;
o=1〜1000である。
kとk’、l、l’、p、p’、q、u、u’、v、v’はそれぞれ、−S−と、−O−、−CH=、=CH−、−CR6=、=CR6−、−C(O)−、−C(C(CN)2)−、−N=、=N−、−NH−、−NR3−、−SiRc=、=SiRc -、−SiR7Rc -から選ばれ;
R6は、それぞれ独立して、a)ハロゲンと、b)−CN、c)−NO2、d)N(Rc)2、e)−ORc、f)−C(O)Rc、g)−C(O)ORc、h)−C(O)N(Rc)2、i)C1-40アルキル基、j)C2-40アルケニル基、k)C2-40アルキニル基、l)C1-40アルコキシ基、m)C1-40アルキルチオ基、n)C1-40ハロアルキル基、o)−Y−C3-14シクロアルキル基、p)−Y−C6-14アリール基、q)−Y−3−14員環シクロヘテロアルキル基、r)−Y−5−14員環ヘテロアリール基から選ばれ、上記C1-40アルキル基とC2-40アルケニル基、C2-40アルキニル基、C3-14シクロアルキル基、C6-14アリール基、3−14員環シクロヘテロアルキル基、Y、Rcは上記定義通りである;
Rcは、上記定義通りであり;
rとsは独立して、−CRcRc−または−C(C(CN)2)−であり;
bは1、2、3、または4である。
Tは、O、S、NH、N−アルキル、N−アリール、N−(アリールアルキル)(例えば、N−ベンジル)、SiH2、SiH−(アルキル)、Si(アルキル)2、SiH−(アリールアルキル)、Si−(アリールアルキル)2、またはSi(アルキル)(アリールアルキル)である。これらヘテロアリール環の例としては、ピロリル、フリル、チエニル、ピリジル、ピリミジル、ピリダジニル、ピラジニル、トリアゾリル、テトラゾリル、ピラゾリル、イミダゾリル、イソチアゾリル、チアゾリル、チアジアゾリル、イソキサゾリル、オキサゾリル、オキサジアゾリル、インドリル、イソインドリル、ベンゾフリル、ベンゾチエニル、キノリル、2−メチルキノリル、イソキノリル、キノキサリル、キナゾリル、ベンゾトリアゾリル、ベンズイミダゾリル、ベンゾチアゾリル、ベンズイソチアゾリル、ベンズイソキサゾリル、ベンズオキサジアゾリル、ベンズオキサゾリル、シノリニル、1H−インダゾリル、2H−インダゾリル、インドリジニル、イソベンゾフリル、ナフチリジニル、フタラジニル、プテリジニル、プリニル、オキサゾロピリジニル、チアゾロピリジニル、イミダゾピリジニル、フロピリジニル、チエノピリジニル、ピリドピリミジニル、ピリドピラジニル、ピリドピリダジニル、チエノチアゾリル、チエノキサゾリル、チエノイミダゾリル基等が含まれる。他のヘテロアリール基の例としては、4,5,6,7−テトラヒドロインドリル、テトラヒドロキノリニル、ベンゾチエノピリジニル、ベンゾフロピリジニル基等が含まれる。いくつかの実施様態においては、本明細書に開示のように、ヘテロアリール基が置換されていてもよい。
アルカリ金属(例えば、Liや、Na、K、Rb、Cs)、アルカリ土類金属(例えば、Caや、Sr、Ba)、O2、XeOF4、(NO2 +)(SbF6 -)、(NO2 +)(SbCl6 -)、(NO2 +)(BF4 -)、AgClO4、H2IrCl6、La(NO3)3、FSO2OOSO2F、Eu、アセチルコリン、R4N+、R4P+、R6As+、R3S+、(式中、Rはアルキル基である)があげられる。
MS(FD、8kV):m/z=465.4g/mol(計算値:C12H2OS2Sn2として465.9g/mol);
1H−NMR(300MHz、CD2Cl2、RT):δ7.28(s、2H)、δ0.41(s、2H);
13C−NMR(75MHz、CD2Cl2、RT):δ148.0、142.0、16.6、−8.0;
元素分析:実測値:30.91%C、4,48%H、13.61%S(計算値:30.94%C、4.33%H、13.77%S)
MS(FD、8kV)m/z=743.3g/mol(計算値:C46H64S4として744.4g/mol);
1H−NMR(250MHz、CD2Cl2,RT):δ7.68(s、2H)、δ7.14(d、J=5.3Hz、2H)、δ7.02(d、J=5.3Hz、2H)、δ2.54(t、J=7.0Hz、4H)、δ1.69(quin、J=7.4Hz、4H)、δ1.6−1.1(m、48H)、δ0.89(t、J=6.5Hz、6H);
13C−NMR(62.5MHz、CD2Cl2、RT):δ140.0、138.99、138.94、132.3、123.7、119.2、117.5、97.4、76.6、32.6、30.4−30.2(複数ピーク)、30.0、29.9、29.7、29.1、23.3、14.5;
元素分析:実測値:74.00%C、8.62%H、17.30%S(計算値:74.14%C、8.66%H、17.21%S)。
MS(FD、8kV)m/z=743.5g/mol(計算値:C46H64S4として744.4g/mol);
1H−NMR(500MHz、C2D2Cl4、60℃):δ7.65(s、2H)、δ7.40(d、J=5.2Hz、2H)、δ7.38(d、J=5.2Hz、2H)、δ3.20(t、J=7.9Hz、4H)、δ1.85(quin、J=7.7Hz、4H)、δ1.56(quin、J=7.6Hz、4H),)、δ1.39(quin、J=7.5Hz、4H);δ1.3−1.1(m、36H)、δ0.82(t、J=7.0Hz、6H);
13C−NMR(125MHz、C2D2Cl4、60℃):δ138.3、136.5、134.2、132.1、131.8、130.0、125.1、125.0、120.8、34.8、32.2、31.3、29.9(複数ピーク)、29.8、29.6、22.9、14.4; 元素分析:実測値:74.12%C、8.67%H、17.04%S(計算値:74.14%C、8.66%H、17.21%S)。
MS(FD、8kV)m/z=1070.1g/mol(計算値:C52H80S4Sn2として1070.3g/mol);
1H−NMR(250MHz、CD2Cl2):δ7.67(s、2H)、δ7.51(s、2H)、δ3.23(t、J=7.7Hz、4H)、δ1.87(quin,、J=7.6Hz、4H)、δ1.59(quin、J=7.4Hz、4H)、δ1.4−1.1(m、40H)、)、δ0.87(t、J=6−5Hz、6H)、δ0.48(s、18H)、
13C−NMR(75MHz、CD2Cl2):δ140.2、139.6、136.8、136.2、134.2、133.2、132.1、129.5、120.4、35.3、32.5、31.7、30.3(複数ピーク)、30.2、29.9、23.3、14.5;
元素分析:実測値:58.84%C、7.66%H、11.38%S(計算値:58.33%C、7.53%H、11.98%S)。
1H−NMR(500MHz、C2D2Cl4、120℃、δ(ppm)):7.6(br、2H)、7.5(br、2H)、7.2(br、2H)。
グローブボックス中で、107.09mg(0.1mmol)の2,8−ビストリメチルスタニル−5,12−ビス(テトラデシル)−ジチエノベンゾ−チエノ[3,2−b]チオフェンと71.68mg(0.1mmol)の5,5’−ジブロモ−4,4’−ジデシル−2,2’−ジチオフェンを、マイクロ波チューブ内の入った1mlのトルエンに溶解する。触媒として5mg(5mmol)のPd(PPh3)4を添加後、このチューブを封じてマイクロ波照射にかける(330W)。温度を120℃で5分間で維持し、次いで140℃でさらに5分間、最後に155℃で40分間維持する。部分的に沈殿したポリマーを1,2−ジクロロベンゼン中に溶解し、メタノールで沈殿化させ、さらに再沈殿させてから、アセトンでのソックスレー抽出に12時間かける。110mgの赤色ポリマーが得られる(85%)。ポリスチレン標準試薬を用いるGPC分析の(1,2,4−トリクロロベンゼン、135℃)結果、Mn=17kg/molであり、Mw=43kg/molであることがわかる。
トランジスタの製作には、熱的に成長させた厚みが200nmの二酸化ケイ素層をもつ、多量にドープしたシリコンウエハーを基材に用いる。気相からヘキサメチルジシラザンを120℃で蒸着させた。この半導体高分子フィルム(約47.5nm厚)は、5mg/mlの1,2−ジクロロベンゼン溶液をスピンコートして(3000rpm、60s)、製造した。基材を100℃で5分間熱処理し、ゆっくりと冷却(1℃/min)後、シャドウマスク越しに半導体薄膜上に金を蒸着させて(3・10-6mbar、1Ås-1、約100nm厚)、ソール電極とドレイン電極を形成して、チャネル長が25〜75であり、幅が約0.5〜1.5mm(W/L=20)である装置を作製した。作製とケースレー4200半導体パラメーター測定装置を用いる電気的測定は、すべて窒素雰囲気下かつ黄灯下で行った。
オンオフ比:Ion/Ioff=3.8(±0.2)・103(五回の測定の平均)
Claims (9)
- 次式のジチエノベンゾ−チエノ[3,2−b]チオフェン−ホモポリマー又はコポリマー:
piは、必要に応じて1〜4個のRa基で置換された単環基または多環基であり、
Raは、それぞれ独立して水素、a)ハロゲン、b)−CN、c)−NO2、d)=O、e)−OH、f)=C(Rb)2、g)C1−20アルキル基、h)C2−20アルケニル基、i)C2−20アルキニル基、j)C1−20アルコキシ基、k)C1−20アルキルチオ基、l)C1−20ハロアルキル基、m)−Y−C3−10シクロアルキル基、n)−Y−C6−14アリール基、o)−Y−3−12員環シクロヘテロアルキル基、またはp)−Y−5−14員環ヘテロアリール基であり(上記のC1−20アルキル基、C2−20アルケニル基、C2−20アルキニル基、C3−10シクロアルキル基、C6−14アリールまたはハロアリール基、3−12員環シクロヘテロアルキル基、5−14員環ヘテロアリール基は、必要に応じて1〜4個のRb基で置換されていてもよい);
Rbは、それぞれ独立して、a)ハロゲン、b)−CN、c)−NO2、d)=O、e)−OH、f)−NH2、g)−NH(C1−20アルキル)、h)−N(C1−20アルキル)2、i)−N(C1−20アルキル)−C6−14アリール、j)−N(C6−14アリール)2、k)−S(O)mH、l)−S(O)m−C1−20アルキル、m)−S(O)2OH、n)−S(O)m−OC1−20アルキル、o)−S(O)m−OC6−14アリール、p)−CHO、q)−C(O)−C1−20アルキル、r)−C(O)−C6−14アリール、s)−C(O)OH、t)−C(O)−OC1−20アルキル、u)−C(O)−OC6−14アリール、v)−C(O)NH2、w)−C(O)NH−C1−20アルキル、x)−C(O)N(C1−20アルキル)2、y)−C(O)NH−C6−14アリール、z)−C(O)N(C1−20アルキル)−C6−14アリール、aa)−C(O)N(C6−14アリール)2、ab)−C(S)NH2、ac)−C(S)NH−C1−20アルキル、ad)−C(S)N(C1−20アルキル)2、ae)−C(S)N(C6−14アリール)2、af)−C(S)N(C1−20アルキル)−C6−14アリール、ag)−C(S)NH−C6−14アリール、ah)−S(O)mNH2、ai)−S(O)mNH(C1−20アルキル)、aj)−S(O)mN(C1−20アルキル)2、ak)−S(O)mNH(C6−14アリール)、al)−S(O)mN(C1−20アルキル)−C6−14アリール、am)−S(O)mN(C6−14アリール)2、an)SiH3、ao)SiH(C1−20アルキル)2、ap)SiH2(C1−20アルキル)、ar)Si(C1−20アルキル)3、as)C1−20アルキル基、at)C2−20アルケニル基、au)C2−20アルキニル基、av)C1−20アルコキシ基、aw)C1−20アルキルチオ基、ax)C1−20ハロアルキル基、ay)C3−10シクロアルキル基、az)C6−14アリールまたはハロアリール基、ba)3−12員環シクロヘテロアルキル基、またはbb)5−14員環ヘテロアリール基であり;
Yは、それぞれ独立して、2価のC1−6アルキレン基、2価のC1−6ハロアルキレン基、または共有結合であり;
下付きmは、それぞれ独立して0、1または2であり;
R1とR2とR3はそれぞれ、独立してH、ハロゲン、CN、C1−30アルキル基、C2−30アルケニル基、C1−30ハロアルキル基、C2−30アルキニル基、C1−30アルコキシ基、C(O)−C1−20アルキル基、C(O)−OC1−20アルキル基、−Y−C3−10シクロアルキル基、−Y−3−12員環シクロヘテロアルキル基(これらはそれぞれ、ハロゲンと−CN、C1−6アルキル基、C1−6アルコキシ基、C1−6ハロアルキル基から選ばれる1〜5個の置換基で置換されていてもよい)、
−L−Ar1、−L−Ar1−Ar1、−L−Ar1−R4、または−L−Ar1−Ar1−R4であり
[式中、Lは、それぞれ独立して、−O−、−Y−O−Y−、−S−、−S(O)−、−Y−S−Y−、−C(O)−、−NRcC(O)−、−NRc−、−SiRc 2−、−Y−[SiRc 2]−Y−、2価のC2−30アルキレン基、2価のC2−30アルケニレン基、2価のC1−30ハロアルキレン基、または共有結合であり
(式中、Rcはそれぞれ、H、C1−20アルキル基、または−Y−C6−14アリール基である);
Ar1は、それぞれ独立して、1価の時はC6−14アリール基または5−14員環ヘテロアリール基であり、2価の時はC6−14アリーレン基または5−14員環ヘテロアリーレン基であり、これらの基は、必要なら
ハロゲンと−CN、C1−6アルキル基、C1−6アルコキシ基、C1−6ハロアルキル基から選ばれる1〜5個の置換基で置換されていてもよい;
R4は、それぞれ独立して、C1−20アルキル基、C2−20アルケニル基、C1−20ハロアルキル基、C1−20アルコキシ基、−L’−Ar2、−L’−Ar2−Ar2、−L’−Ar2−R5、または−L’−Ar2−Ar2−R5である
(式中、L’は、それぞれ独立して、−O−、−Y−O−Y−、−S−、−S(O)−、−Y−S−Y−、−C(O)−、−NRcC(O)−、−NRc−、−SiRc 2−、−Y−[SiRc 2]−Y−、2価のC1−20アルキル基、2価のC1−20アルケニル基、2価のC1−20ハロアルキル基、または共有結合であり;
Ar2は、それぞれ独立して、1価の時はC6−14アリール基または5−14員環ヘテロアリール基であり、2価の時はC6−14アリーレン基または5−14員環ヘテロアリーレン基であり、各基は必要に応じて
ハロゲンと−CN、C1−6アルキル基、C1−6アルコキシ基、C1−6ハロアルキル基から選ばれる1〜5個の置換基で置換されていてもよい;
R5はそれぞれ、C1−20アルキル基、C2−20アルケニル基、C1−20ハロアルキル基、またはC1−20アルコキシ基であり;
Yは、それぞれ独立して、2価のC1−6アルキレン基、2価のC1−6ハロアルキレン基、または共有結合である)];
下付きnは0、1、2であり;
下付きoは1〜1000である。]
- 一種以上の請求項1に記載のポリマーが液状媒体に溶解あるいは分散した組成物。
- 一種以上の請求項1に記載のポリマーを含む薄膜半導体。
- 基材と、該基材上に形成された請求項3に記載の薄膜半導体とからなる複合物。
- 請求項4に記載の複合物の製造方法であって、請求項1に記載のポリマーを液状媒体中に溶解または分散させて溶液をつくり、該溶液を基材上に塗布し、溶媒を除去して前記基材上の薄膜半導体を形成する方法。
- 上記溶液が、スピンコーティング、ドロップキャスティング、浸漬塗装、または印刷により塗布される請求項5に記載の方法
- 請求項3の薄膜半導体または請求項4の複合物を含む電界効果トランジスタ装置。
- 請求項3の薄膜半導体または請求項4の複合物を含む光起電装置。
- 請求項3の薄膜半導体または請求項4の複合物を含む有機発光ダイオード装置。
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