JP5841528B2 - 縮合チオフェン、その物品および方法 - Google Patents
縮合チオフェン、その物品および方法 Download PDFInfo
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- JP5841528B2 JP5841528B2 JP2012513235A JP2012513235A JP5841528B2 JP 5841528 B2 JP5841528 B2 JP 5841528B2 JP 2012513235 A JP2012513235 A JP 2012513235A JP 2012513235 A JP2012513235 A JP 2012513235A JP 5841528 B2 JP5841528 B2 JP 5841528B2
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
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- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 3
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
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- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
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- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Chemical class C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 2
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- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- GPZGAMSKANHWHO-UHFFFAOYSA-N trimethyl-(4-trimethylstannylphenyl)stannane Chemical compound C[Sn](C)(C)C1=CC=C([Sn](C)(C)C)C=C1 GPZGAMSKANHWHO-UHFFFAOYSA-N 0.000 description 2
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- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- MGYMXDNDDXJPHB-UHFFFAOYSA-N 2,6-bis[2-(4-pentylphenyl)ethenyl]anthracene Chemical compound C1=CC(CCCCC)=CC=C1C=CC1=CC=C(C=C2C(C=CC(C=CC=3C=CC(CCCCC)=CC=3)=C2)=C2)C2=C1 MGYMXDNDDXJPHB-UHFFFAOYSA-N 0.000 description 1
- OQOLNSMRZSCCFZ-UHFFFAOYSA-N 9,10-bis(2-phenylethenyl)anthracene Chemical compound C=1C=CC=CC=1C=CC(C1=CC=CC=C11)=C2C=CC=CC2=C1C=CC1=CC=CC=C1 OQOLNSMRZSCCFZ-UHFFFAOYSA-N 0.000 description 1
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- ALMFIOZYDASRRC-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(C(F)(F)F)C=C1 ALMFIOZYDASRRC-UHFFFAOYSA-N 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Description
「FTx」は、xが、縮合チオフェン環または1つのコアユニットに縮合された環状ユニットの数を表す整数である、縮合チオフェンを称する。例えば、FT2はコアユニット中に2つの縮合環を有し、FT3はコアユニット中に3つの縮合環を有し、FT4はコアユニット中に4つの縮合環を有し、FT5はコアユニット中に5つの縮合環を有し、以下同様にコアユニットにおける数が増えていく。
各Rが、独立して、例えば、nが2から4までの場合、炭素−炭素結合、炭素−硫黄結合、または溶解度増強置換基、例えば、−OR、−SR、ポリエーテル、ポリチオエーテル、および同様の基などの、酸素または硫黄置換−R置換基を含む置換または未置換の(C1-24)ヒドロカルビルであり、
nが2から4までの整数であり、
各−G1が、独立して、
例えば、nが2から4までの場合、炭素−炭素結合または炭素−硫黄結合、
式−{Ar(R1)q}p−Ar(R1)qの一価の置換または未置換アリール、
式−{Het(R1)q}p−Het(R1)qの一価の置換または未置換ヘテロアリール、または
−Het−Ar、−Ar−Het、−Het(R1)q−Ar、−Ar−Het(R1)q、−Het(R1)q−Ar(R1)q、および同様の組合せなどの式−{Ar(R1)q}p−Ar(R1)q、または−{Het(R1)q}p−Het(R1)qの1つ以上の置換または未置換アリールおよびヘテロアリール置換基の一価の組合せ、
であり、
pが0から4までであり、
qが0から4までであり、
各−R1が、独立して、−H、−F、または一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビル、またはそれらの組合せ、およびその塩である、
化合物を提供する。
各R2は、独立して、H、または一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビル、または−Ar、−F、もしくはそれらの組合せであり、
R3は、H、または一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビルであり、
sは、0から5までの整数である。
R2の例は、−(C1-24)ヒドロカルビル、−(C1-10)アルコキシル、−{(C1-10)アルコキシル}t−H、−オキシアルキレン、−(オキシヒドロカルビレン)tH、−Ar、および同様の置換基のいずれであっても差し支えなく、ここで、tは1から10までである。
4,11−ビス(チオフェン−2−イル)−5,12−ジトリデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン;
4,11−ビス(チオフェン−2−イル)−5,12−ジヘプタデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン;
6,14−ビス(チオフェン−2−イル)−5,15−ジトリデシル−3,7,10,13,17−ペンタチアペンタシクロ[9.6.0.02,9.04,8.012,16]ヘプタデカ−1(11),2(9),4(8),5,12(16),14−ヘキサエン;
4,11−ジフェニル−5,12−ジトリデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン;
6,14−ジフェニル−5,15−ジトリデシル−3,7,10,13,17−ペンタチアペンタシクロ[9.6.0.02,9.04,8.012,16]ヘプタデカ−1(11),2(9),4(8),5,12(16),14−ヘキサエン;
4,11−ビス(4−トリフルオロメチルフェニル)−5,12−ジヘプタデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン;または
4,11−ジフェニル−5,12−ジヘプタデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン;およびその塩、またはそれらの混合物が挙げられる。
このX−C−X生成物を、少なくとも2モル当量の式M−G1のカップリング化合物および金属触媒と接触させて、式G1−C−G1のα−,α’−二置換生成物を形成する、
各工程を有してなる方法を提供する。
−G1は、例えば、
各R2は、独立して、H、または一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビル、−Ar、−F、またはここに定義された同様の置換基、もしくはそれらの組合せであり、
R3は、H、または一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビルであり、
sは、0から5までの整数である。
各Rは、独立して、炭素−炭素結合、炭素−硫黄結合、または置換または未置換の(C1-24)ヒドロカルビルであり、
nは2から4までの整数であり、
mは、中間の値と範囲を含む、2から10,000までの整数であり、
各G1は、独立して、
炭素−炭素結合または炭素−硫黄結合、
式−{Ar(R1)q}p−Ar(R1)q−の二価の置換または未置換のアリール、または
式−{Het(R1)q}p−Het(R1)q−の二価の置換または未置換のヘテロアリール、
であり、
各−R1は、独立して、−H、−F、もしくは一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビル、またはそれらの組合せ、およびその塩であり、
各G2が、独立して、
式−{Ar(R1)q}p−Ar(R1)q−の二価の置換または未置換のアリール、
式−{Het(R1)q}p−Het(R1)q−の二価の置換または未置換のヘテロアリール、または
ビニルまたはアセチレニルなどの、二価の置換または未置換の不飽和の(C1-24)ヒドロカルビル
であり、
各pは独立して0から4までであり、
各qは独立して0から4までであり、
各−R1は、独立して、独立して、−H、−F、もしくは一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビル、またはそれらの組合せ、およびその塩である、
ポリマーを提供する。
このX−G1−C−G1−X生成物を、約1モル当量比の式M−G2−Mのカップリング化合物および金属触媒と接触させて、前記ポリマーを形成する、
各工程を有してなる方法を提供する。
各R2は、独立して、H、または一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビル、−Ar、−F、またはここに定義された同様の置換基、もしくはそれらの組合せであり、
R3は、H、または一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビルであり、
sは、0から5までの整数であり、金属触媒はPd(PPh3)4である。
このX−C−X生成物を、例えば、約0.8から約1.2モル当量比、約0.9から約1.1モル当量比、好ましくは約1.0モル当量比、すなわち、1:1のモル当量比である約1モル当量比の式M−G1−G2−G1−Mのカップリング化合物および金属触媒と接触させて、式:
ここで、各Rが、独立して、一価の置換または未置換の(C1-24)ヒドロカルビルであり、nが0から4までの整数であり、mが2から10,000までの整数であるポリマー生成物を形成する、
各工程を有してなる方法を提供する。
各G1およびG2は、独立して、例えば、
各R2は、独立して、H、または一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビル、−Ar、−F、およびここに定義された同様の置換基、またはそれらの組合せであり、
R3は、H、または一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビルであり、
sは、0から5までの整数であり、金属触媒はPd(PPh3)4である。
各−G1−は、独立して、
式−{Ar(R1)q}p−Ar(R1)q−の二価の置換または未置換のアリール、または
式−{Het(R1)q}p−Het(R1)q−の二価の置換または未置換のヘテロアリール、
であり、
各−R1は、独立して、−H、−F、もしくは一価の置換または未置換、飽和または不飽和の(C1-24)ヒドロカルビル、またはそれらの組合せ、およびその塩であり、
各pは独立して0から4までであり、
各qは独立して0から4までであり、
各Xは独立してハロ、またはその塩、もしくはそれらの混合物である。
4,11−ビス(5−ブロモチオフェン−2−イル)−5,12−ジトリデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン(7)、および
6,14−ビス(5−ブロモチオフェン−2−イル)−5,15−ジトリデシル−3,7,10,13,17−ペンタチアペンタシクロ[9.6.0.02,9.04,8.012,16]ヘプタデカ−1(11),2(9),4(8),5,12(16),14−ヘキサエン(9);
の対応する化学名を有する、式(7)および(9):
henyl-dithieno[3,2-b:2',3'-d]thiophene Semiconductor and Polymer Gate Dielectric; Melucci, M. et al., Chemistry--A European Journal, (2007), 13(36), 10046-10054, Liquid-Crystalline Rigid-Core Semiconductor Oligothiophenes: Influence of Molecular Structure on Phase Behaviour and Thin-Film Propertiesを参照のこと)としての潜在的な用途について報告されてきた。意外なことに、α−,β−置換FT4、FT5、またはFT6化合物の例は報告されていない。これは、α−,β−置換FT4、FT5、またはFT6化合物の不十分な溶解度のせいであるかもしれず、このことは、さらなる構造的修飾を難しくし得る。
高度に規則的なまたは反復構造を有する新規のポリマー構造を製造するために、ポリマーにおけるマーまたはユニットの1つ以上を合成的に操作できるまたは体系的に変化させられる単純さまたは容易さ、
開示されたポリマー調製方法は、追加の柔軟性またはポリマー構造の部位規則性を指定する能力を提供すること、および
開示された方法を使用して、少ない工程および少ない試薬などで、公知のポリマー(例えば、同一出願人の同時係属出願である米国特許出願第61/072468号明細書を参照のこと)をより効率的に製造できること、
を含む利点を提供する。
デバイスの製造および特徴付け 有機半導体チャンネルとしてポリマー10を使用した全上面接触下面ゲートトランジスタを空気中で製造した。ゲート電極としてSi<100>ウェハーを、ゲート誘電体として二酸化ケイ素を使用した。1,2−ジクロロベンゼン中の10に基づくOFETデバイスを、オクチルトリクロロシラン(C8OTS)蒸気処理したSi/SiO2ウェハー上に製造した。OFETデバイスを調製するための一般手法および例えば、移動度を測定するための方法が、例えば、J. Amer. Chem. Soc., 2008, 130, 13202-13203に開示されている。ポリマー10のデバイスの代表的な電流−電圧曲線が図1に示されている。
選択されたFT4およびFT5化合物の溶解度 表1は、いくつかのα−,α’−未置換,β−,β’−アルキル置換FT4(およびFT5)の、いくつかのα−,α’−置換,β−,β’−アルキル置換FT4(およびFT5)化合物との溶解度比較を提供する。
一般手法:10mgのFT4またはFT5化合物を5.0mLの特定の溶媒と混合し、次いで、ネジ蓋式ガラス製バイアル内に密閉した。その結果として生じた混合物を周囲温度で30分間に亘り超音波浴中に保持し、次いで、30分間に亘り静止状態に維持して、透明な溶液が形成されたか否かを調べた。このような60分後に混合物がまだ透明でない場合、バイアルに同じ溶媒をさらに5.0mL加え、合計で20mLの溶媒となるまで、60分間の混合と放置の手法を繰り返した。
Claims (8)
- 4,11−ビス(チオフェン−2−イル)−5,12−ジトリデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン;
4,11−ビス(チオフェン−2−イル)−5,12−ジヘプタデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン;
6,14−ビス(チオフェン−2−イル)−5,15−ジトリデシル−3,7,10,13,17−ペンタチアペンタシクロ[9.6.0.02,9.04,8.012,16]ヘプタデカ−1(11),2(9),4(8),5,12(16),14−ヘキサエン;
4,11−ジフェニル−5,12−ジトリデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン;
6,14−ジフェニル−5,15−ジトリデシル−3,7,10,13,17−ペンタチアペンタシクロ[9.6.0.02,9.04,8.012,16]ヘプタデカ−1(11),2(9),4(8),5,12(16),14−ヘキサエン;
4,11−ビス(4−トリフルオロメチルフェニル)−5,12−ジヘプタデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン;または
4,11−ジフェニル−5,12−ジヘプタデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン;
およびその塩から選択される請求項2記載の化合物、あるいはその混合物。 - 式
X−G1−C−G1−X
のジハロゲン化化合物、またはその塩:
ここで、
Cは式:
各−G1−は、独立して、
式−{Ar(R1)q}p−Ar(R1)q−の二価の置換または未置換のアリール(ここで、Arはアリールである)、または
式−{Het(R1)q}p−Het(R1)q−の二価の置換または未置換のヘテロアリール(ここで、Hetはヘテロアリールである)、またはそれらの組合せであり、
各Rは、独立して、一価の置換または未置換の(C1-24)ヒドロカルビルであり、
各−R1は、独立して、−H、−F、もしくは一価の置換または未置換の飽和または不飽和の(C1-24)ヒドロカルビルであり、
各nは独立して2から4までの整数であり、
各pは独立して0から4までであり、
各qは独立して0から4までであり、
各Xは独立してハロである。 - 式
X−G1−C−G1−X
の化合物が、
4,11−ビス(5−ブロモチオフェン−2−イル)−5,12−ジトリデシル−3,7,10,14−テトラチアテトラシクロ[6.6.0.02,6.09,13]テトラデカ−1(8),2(6),4,9(13),11−ペンタエン(7)、または
6,14−ビス(5−ブロモチオフェン−2−イル)−5,15−ジトリデシル−3,7,10,13,17−ペンタチアペンタシクロ[9.6.0.02,9.04,8.012,16]ヘプタデカ−1(11),2(9),4(8),5,12(16),14−ヘキサエン(9)、
であることを特徴とする請求項5記載のハロゲン化化合物。 - 式:
式:
該X−C−X生成物を、少なくとも2モル当量比の式M−G1のカップリング化合物および金属触媒と接触させて、式G1−C−G1のα−,α’−二置換生成物を形成する、
各工程を有してなり、
Mは、−SnR4 3、−B(OH)2、−B(OR4)2、−B(シクロ−OR4O−)、または−MgX、もしくはそれらの組合せを有し、ここで、Xはハロゲンであり、各R4は、独立して、一価の置換または未置換の(C1-24)ヒドロカルビルである、方法。
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US8217183B2 (en) | 2010-05-18 | 2012-07-10 | Corning Incorporated | Methods of making fused thiophenes |
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