JP2012235075A - 有機半導体 - Google Patents
有機半導体 Download PDFInfo
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- JP2012235075A JP2012235075A JP2011104618A JP2011104618A JP2012235075A JP 2012235075 A JP2012235075 A JP 2012235075A JP 2011104618 A JP2011104618 A JP 2011104618A JP 2011104618 A JP2011104618 A JP 2011104618A JP 2012235075 A JP2012235075 A JP 2012235075A
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- organic semiconductor
- alkoxy group
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- halogen
- alkyl group
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 81
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
- 229910052786 argon Inorganic materials 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 150000001923 cyclic compounds Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 238000001894 space-charge-limited current method Methods 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 abstract description 8
- 238000000576 coating method Methods 0.000 abstract description 8
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 239000010408 film Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000012300 argon atmosphere Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000001226 reprecipitation Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- GSRVZUVLHFUNRO-UHFFFAOYSA-N 4-[4-(4-pentoxyphenyl)phenyl]benzaldehyde Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(C=2C=CC(C=O)=CC=2)C=C1 GSRVZUVLHFUNRO-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920000144 PEDOT:PSS Polymers 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XSGGLCGBXDPDLL-UHFFFAOYSA-N 1-bromo-4-(4-pentoxyphenyl)benzene Chemical group C1=CC(OCCCCC)=CC=C1C1=CC=C(Br)C=C1 XSGGLCGBXDPDLL-UHFFFAOYSA-N 0.000 description 3
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000547 conjugated polymer Polymers 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- ARUBXNBYMCVENE-UHFFFAOYSA-N 4-(4-bromophenyl)phenol Chemical group C1=CC(O)=CC=C1C1=CC=C(Br)C=C1 ARUBXNBYMCVENE-UHFFFAOYSA-N 0.000 description 1
- YAPVGSXODFOBBR-UHFFFAOYSA-N 4-pentoxybenzaldehyde Chemical compound CCCCCOC1=CC=C(C=O)C=C1 YAPVGSXODFOBBR-UHFFFAOYSA-N 0.000 description 1
- 0 C*C(c(cc1)ccc1-c(cc1)ccc1-c1ccc(*)cc1)=C(C=C1)SC1=C(C=C1)SC1=C(c1ccc(-c2ccc(C(C)(C)C)[s]2)[s]1)c(cc1)ccc1-c(cc1)ccc1-c1ccc(*)cc1 Chemical compound C*C(c(cc1)ccc1-c(cc1)ccc1-c1ccc(*)cc1)=C(C=C1)SC1=C(C=C1)SC1=C(c1ccc(-c2ccc(C(C)(C)C)[s]2)[s]1)c(cc1)ccc1-c(cc1)ccc1-c1ccc(*)cc1 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MWVNSXPNTJYJDR-DHIUTWEWSA-N n-[(2r,4r)-1,4-dihydroxy-4-phenylbutan-2-yl]tetradecanamide Chemical group CCCCCCCCCCCCCC(=O)N[C@@H](CO)C[C@@H](O)C1=CC=CC=C1 MWVNSXPNTJYJDR-DHIUTWEWSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229930192474 thiophene Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- 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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Photovoltaic Devices (AREA)
- Thin Film Transistor (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
本実施の形態の有機半導体は、下記式(1)で表される繰り返し単位を有し、イオン化ポテンシャルが5.0eVより大きいことを特徴とする。なお、イオン化ポテンシャルは、有機半導体の真空準位を0eVとしたときの値である。式(1)中、Ar及びAr’は互いに同一または異なり、独立して共役構造を有する環状の化合物である。また、R及びR’は互いに同一または異なり、独立して直鎖アルキル基、分岐アルキル基、直鎖アルコキシ基、分岐アルコキシ基、水素、ハロゲンのいずれかである。また、R’’は直鎖アルキル基、分岐アルキル基、直鎖アルコキシ基、分岐アルコキシ基、水素、ハロゲンのいずれかである。また、x、yおよびzは0.5の倍数であり、x≦z、y≦zである。また、nは1〜1000の定数である。
実施例1と比較例1〜2で用いた各有機半導体の合成方法について以下に説明する。
実施例1で用いられる有機半導体1−1qを下記反応式に従って合成した。
比較例1で用いられる有機半導体1−2qを下記反応式に従って合成した。
比較例2で用いられる有機半導体1−3qを下記反応式に従って合成した。
SCLC法による正孔移動度は以下のように求められた値である。ITO透明電極の上に、市販のPEDOT:PSS(商品名 Starck AI 4083)をスピン塗布により製膜した後、120〜150℃で加熱し乾燥させて膜厚約40nmのPEDOT:PSS膜を形成した。所定量の当該有機半導体をクロロベンゼン溶媒に加えて塗布液を作成し、この塗布液をPEDOT:PSS膜の上にスピン塗布した。この後、所定の温度で乾燥させて膜厚約130nmの有機半導体層を形成した。得られた有機半導体層の上に、真空蒸着法により膜厚が100nmになるようにAuを成膜した。成膜速度は1秒当たりに0.01nmを超えないように調整した。作製した素子(ITO透明電極/PEDOT:PSS膜/光電変換層/Au)を暗箱内入れて、電流(J)−電圧(V)特性を測定した。得られた電流−電圧特性をJ^1/2を縦軸、Vを横軸にlog-logプロットした後、SCLC領域にてフィッティングして傾き(a)を算出した。次に、(J)^1/2={9ε0εrμ/8(L^3)}^1/2 V式から、{9ε0εrμ/8(L^3) }^1/2の部分がグラフから求めた傾きに等しいため、a={9ε0εrμ/8(L^3) }^1/2となる。これをμについて解き直し、μ={8(L^3)( a^2)}/{9ε0εr}、として、これに0,εrを代入して算出した。μは有機半導体の移動度、Lは有機半導体の膜厚、ε0は真空の誘電率、εrは有機半導体の誘電率である。
当該有機半導体の真空準位を0eVにした時のイオン化ポテンシャルは、理研計器株式会社大気中光電子分光機 AC-3(登録商標)を用いて測定した値である。なお、イオン化ポテンシャル評価用のサンプルは以下の方法で作製した。窒素雰囲気下、所定量の当該重合体をクロロベンゼン溶媒1mLに加えて塗布液を作成し、この塗布液を基板の上にスピン塗布した。この後、所定の温度で乾燥させて膜厚約120nmの層を形成した。
溶解度とは以下のように求められた値である。窒素雰囲気下、所定量の当該有機半導体とクロロベンゼン1mLを蓋付サンプル瓶に加え、10分間撹拌後、10分間放置し、目視で沈殿が発生しない重量である。
実施例1および比較例1〜2の各有機半導体について、クロロベンゼン1mLに対する溶解度、正孔移動度およびイオン化ポテンシャルを測定した結果を表1に示す。
Claims (7)
- 前記式(1)中、Ar及びAr’は置換基を有するアリーレン基またはヘテロアリーレン基である請求項1記載の有機半導体。
- 前記式(1)中、R及びR’は、直鎖アルキル基、分岐アルキル基、水素、ハロゲンのいずれかである請求項1に記載の有機半導体。
- 前記式(1)中、R’’は直鎖アルコキシ基、分岐アルコキシ基、ハロゲンのいずれかである請求項1に記載の有機半導体。
- 前記式(1)中、nは5〜1000である請求項1に記載の有機半導体。
- SCLC法で測定した前記有機半導体のホール移動度が3.0×10−5cm2/Vs以上である請求項1乃至5のいずれか1項に記載の有機半導体。
- クロロベンゼン1mLに対する前記有機半導体の溶解度が25mg以上である請求項1乃至6のいずれか1項に記載の有機半導体。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2011104618A JP5650051B2 (ja) | 2011-05-09 | 2011-05-09 | 有機半導体 |
CN201280022464.1A CN103563114B (zh) | 2011-05-09 | 2012-05-07 | 有机半导体 |
EP12782276.5A EP2709180A4 (en) | 2011-05-09 | 2012-05-07 | ORGANIC SEMICONDUCTOR |
PCT/JP2012/002989 WO2012153511A1 (ja) | 2011-05-09 | 2012-05-07 | 有機半導体 |
TW101116320A TW201307361A (zh) | 2011-05-09 | 2012-05-08 | 有機半導體 |
US14/074,799 US8981120B2 (en) | 2011-05-09 | 2013-11-08 | Organic semiconductor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2011104618A JP5650051B2 (ja) | 2011-05-09 | 2011-05-09 | 有機半導体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012235075A true JP2012235075A (ja) | 2012-11-29 |
JP5650051B2 JP5650051B2 (ja) | 2015-01-07 |
Family
ID=47138999
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011104618A Expired - Fee Related JP5650051B2 (ja) | 2011-05-09 | 2011-05-09 | 有機半導体 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8981120B2 (ja) |
EP (1) | EP2709180A4 (ja) |
JP (1) | JP5650051B2 (ja) |
CN (1) | CN103563114B (ja) |
TW (1) | TW201307361A (ja) |
WO (1) | WO2012153511A1 (ja) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000143777A (ja) * | 1998-11-16 | 2000-05-26 | Japan Science & Technology Corp | 光学活性高分子とその製造方法 |
JP2004186695A (ja) * | 2002-12-04 | 2004-07-02 | Merck Patent Gmbh | モノ、オリゴおよびポリビス(チエニル)アリーレン並びに電荷移動材料としてのこれらの使用 |
JP2011505681A (ja) * | 2007-11-01 | 2011-02-24 | エイチ・シー・スタルク・クレビオス・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 非極性芳香族ポリマーを含む層をコーティングするためのプロセス |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE602004017550D1 (de) | 2003-08-28 | 2008-12-18 | Merck Patent Gmbh | Mono-, Oligo- und Polythienoi2,3-b thiophene |
CN101570533A (zh) * | 2004-02-25 | 2009-11-04 | 默克专利股份有限公司 | 反应性介晶型电荷输运化合物 |
CN100585902C (zh) * | 2005-09-21 | 2010-01-27 | 三菱化学株式会社 | 有机半导体材料和有机场效应晶体管 |
JP2008106239A (ja) | 2006-09-26 | 2008-05-08 | Sumitomo Chemical Co Ltd | 有機光電変換素子及びその製造に有用な重合体 |
US20100084000A1 (en) | 2006-09-26 | 2010-04-08 | Sumitomo Chemical Company, Limited | Organic photoelectric conversion device and polymer useful for producing the same |
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2011
- 2011-05-09 JP JP2011104618A patent/JP5650051B2/ja not_active Expired - Fee Related
-
2012
- 2012-05-07 CN CN201280022464.1A patent/CN103563114B/zh not_active Expired - Fee Related
- 2012-05-07 WO PCT/JP2012/002989 patent/WO2012153511A1/ja active Application Filing
- 2012-05-07 EP EP12782276.5A patent/EP2709180A4/en not_active Withdrawn
- 2012-05-08 TW TW101116320A patent/TW201307361A/zh unknown
-
2013
- 2013-11-08 US US14/074,799 patent/US8981120B2/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000143777A (ja) * | 1998-11-16 | 2000-05-26 | Japan Science & Technology Corp | 光学活性高分子とその製造方法 |
JP2004186695A (ja) * | 2002-12-04 | 2004-07-02 | Merck Patent Gmbh | モノ、オリゴおよびポリビス(チエニル)アリーレン並びに電荷移動材料としてのこれらの使用 |
JP2011505681A (ja) * | 2007-11-01 | 2011-02-24 | エイチ・シー・スタルク・クレビオス・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 非極性芳香族ポリマーを含む層をコーティングするためのプロセス |
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US8981120B2 (en) | 2015-03-17 |
EP2709180A4 (en) | 2014-10-22 |
CN103563114A (zh) | 2014-02-05 |
CN103563114B (zh) | 2016-06-01 |
TW201307361A (zh) | 2013-02-16 |
US20140114078A1 (en) | 2014-04-24 |
JP5650051B2 (ja) | 2015-01-07 |
EP2709180A1 (en) | 2014-03-19 |
WO2012153511A1 (ja) | 2012-11-15 |
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